N-methyl-2-pyrrolidone → N-[6-(azetidin-1-yl)-3-pyridinyl]-3-diethylsilyl-1-[(3-fluorophenyl)methyl]-5-methylindole-2-carboxamide

HRID 1948802Notes

Reaction equation

HRID 1948802 reaction equation
[N:1]1([C:5]2[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]3[N:15]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)[C:16]4[C:21]([CH:22]=3)=[CH:20][C:19](Br)=[CH:18][CH:17]=4)=[O:13])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:32]([SiH:34]([CH2:36][CH3:37])C)[CH3:33].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].[CH3:56]N1CCCC1=O>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[N:1]1([C:5]2[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]3[N:15]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)[C:16]4[C:21]([C:22]=3[SiH:34]([CH2:36][CH3:37])[CH2:32][CH3:33])=[CH:20][C:19]([CH3:56])=[CH:18][CH:17]=4)=[O:13])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 61695Pentapotassium TriphosphateHCID 69799Diethyl(methyl)silaneHCID 66850586HCID 66850586, compound

Product 1

HCID 131730345N-[6-(azetidin-1-yl)-3-pyridinyl]-3-diethylsilyl-1-[(3-fluorophenyl)methyl]-5-methylindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Compound No. 22 was prepared according to a process similar to that described in stage 8.4, by reacting 0.15 g (0.31 mmol) of N-[6-(azetidin-1-yl)pyridin-3-yl]-5-bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in stage 17.3, with 95 mg (0.93 mmol) of diethyl(methyl)silane in the presence of 0.2 g (0.94 mmol) of potassium triphosphate and of 16 mg (0.03 mmol) of bis(tri-tert-butylphosphine)palladium in 2 ml of dry 1-methyl-2-pyrrolidinone (NMP). 13 mg of the expected product are obtained.

Workup

  1. custom22 was prepared
  2. customprepared

Sources & evidence

ORD record
ord-69194d69e8d64a27b65782342fbc3b5a
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

Loading…