Serendipitous base catalysed condensation-heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles.
Dudhe, Premansh; Venkatasubbaiah, Krishnan; Pathak, Biswarup; Chelvam, Venkatesh; Organic & biomolecular chemistry 18 (2020) 1582–1587; doi:10.1039/c9ob02657f

data_7157344
_publ_section_title
;
 Serendipitous base catalysed condensation-heteroannulation of
 iminoesters: a regioselective route to the synthesis of 4,6-disubstituted
 5-azaindoles.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1582
_journal_page_last               1587
_journal_paper_doi               10.1039/c9ob02657f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C27 H23 N3 O2'
_chemical_formula_sum            'C27 H23 N3 O2'
_chemical_formula_weight         838.93
_chemical_melting_point          408.0(10)
_chemical_name_common            5-Azaindole
_chemical_name_systematic
'methyl 1-benzyl-4-(1-benzyl-1H-pyrrol-2-yl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate'
_chemical_properties_physical    Stable
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-04-13 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                79.390(3)
_cell_angle_beta                 89.757(2)
_cell_angle_gamma                77.142(3)
_cell_formula_units_Z            2
_cell_length_a                   11.1329(4)
_cell_length_b                   11.9307(5)
_cell_length_c                   17.5044(7)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.28
_cell_volume                     2226.30(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30867
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.039
_diffrn_reflns_theta_min         1.184
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0747 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8994. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'Yellow Crystalline Solid'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       irregular
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2 and Hexane'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         9679
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1157P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4754
_reflns_number_total             9679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02657f2.cif
_cod_data_source_block           kv_nph2phi_bme_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '407-409' was changed to
'408.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157344.cif.
;
_cod_database_code               7157344
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-C23
 1.37 with sigma of 0.002
 C23-C24
 1.37 with sigma of 0.002
 C22-C21
 1.37 with sigma of 0.002
 C21-C20
 1.37 with sigma of 0.002
 C20-C25
 1.37 with sigma of 0.002
 C25-C24
 1.37 with sigma of 0.002
3. Others
 Fixed Sof: C43(0.7) C44(0.7) C45(0.7) C45A(0.3) C46A(0.3) C47A(0.3) C17(0.4)
 C17A(0.6)
4.a Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C46(H46A,H46B), C12(H12A,H12B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C52(H52), C51(H51), C50(H50), C41(H41), C36(H36), C37(H37), C38(H38),
 C30(H30), C33(H33), C34(H34), C49(H49), C48(H48), C15(H15), C14(H14), C3(H3),
 C9(H9), C10(H10), C11(H11), C6(H6), C7(H7), C21(H21), C25(H25), C23(H23),
 C24(H24), C22(H22)
4.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              60205
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'