Facile synthesis of 4- and 7-azaindoles from the corresponding imines by palladium-catalyzed cascade C-C and C-N coupling.
Pham, Ngo Nghia; Dang, Thanh Tuan; Ngo, Ngoc Thang; Villinger, Alexander; Ehlers, Peter; Langer, Peter; Organic & biomolecular chemistry 13 (2015) 6047–6058; doi:10.1039/c5ob00720h

data_7154441
_publ_section_title
;
 Facile synthesis of 4- and 7-azaindoles from the corresponding imines by
 palladium-catalyzed cascade C-C and C-N coupling.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6047
_journal_page_last               6058
_journal_paper_doi               10.1039/c5ob00720h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_chemical_name_systematic
;
1-(4-Methoxyphenyl)-2-phenyl-1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-28 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.98960(10)
_cell_length_b                   11.3423(2)
_cell_length_c                   11.1347(2)
_cell_measurement_reflns_used    6394
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      2.57
_cell_volume                     751.86(2)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.497
_diffrn_reflns_theta_min         2.571
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.7229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.1180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4806
_reflns_number_total             5379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00720h2.cif
_cod_data_source_block           is_pham1591
_cod_depositor_comments
'Adding full bibliography for 7154440--7154442.cif.'
_cod_database_code               7154441
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-4
_shelx_res_checksum              3912