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_7154440
_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_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_chemical_name_systematic
;
2-(4-Methoxyphenyl)-1-phenyl-1<i>H</i>-pyrrolo[3,2-<i>b</i>]pyridine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                74.9510(10)
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_cell_angle_gamma                84.4900(10)
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_cell_measurement_temperature    173(2)
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_cell_measurement_theta_min      2.49
_cell_volume                     1544.18(5)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
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_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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
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_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_exptl_crystal_size_max          0.290
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_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         11167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0453P)^2^+0.4232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8411
_reflns_number_total             11167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00720h2.cif
_cod_data_source_block           is_pham1482
_cod_depositor_comments
'Adding full bibliography for 7154440--7154442.cif.'
_cod_database_code               7154440
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
_shelx_res_checksum              57109