Palladium-Catalyzed Regioselective Arylation of Pyrazolo[1,5-a]pyridines via C–H Activation and Synthetic Applications on P38 Kinase Inhibitors
Wu, Hung-Chou; Chu, Jean-Ho; Li, Chin-Wei; Hwang, Long-Chih; Wu, Ming-Jung; Organometallics 35 (2016) 288–; doi:10.1021/acs.organomet.5b00988

data_4088283
_publ_section_title
;
 Palladium-Catalyzed Regioselective Arylation of Pyrazolo[1,5-a]pyridines
 via C--H Activation and Synthetic Applications on P38 Kinase Inhibitors
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              288
_journal_paper_doi               10.1021/acs.organomet.5b00988
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C13 H9 Cl N2'
_chemical_formula_sum            'C13 H9 Cl N2'
_chemical_formula_weight         228.67
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.485(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6083(9)
_cell_length_b                   11.4037(8)
_cell_length_c                   7.3882(6)
_cell_measurement_reflns_used    6600
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      1.63
_cell_volume                     1055.49(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6600
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.8903
_exptl_absorpt_correction_T_min  0.8040
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.1403P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                2994
_reflns_number_total             3127
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00988_si_002.cif
_cod_data_source_block           a11570
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4088283