N-methyl-2-pyrrolidone → N-[6-(azetidin-1-yl)-3-pyridinyl]-3-dimethylsilyl-1-[(3-fluorophenyl)methyl]-5-propan-2-ylindole-2-carboxamide

HRID 1948801Notes

Reaction equation

HRID 1948801 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.[CH3:32][SiH:33]([CH3:37])C(C)C.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].CN1C[CH2:60][CH2:59][C:58]1=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:33]([CH3:37])[CH3:32])=[CH:20][C:19]([CH:59]([CH3:60])[CH3:58])=[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 4133535Dimethyl(1-methylethyl)silaneHCID 66850586HCID 66850586, compound

Product 1

HCID 131730344N-[6-(azetidin-1-yl)-3-pyridinyl]-3-dimethylsilyl-1-[(3-fluorophenyl)methyl]-5-propan-2-ylindole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Compound No. 21 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 dimethyl(isopropyl)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). 23 mg of the expected product are obtained.

Workup

  1. custom21 was prepared
  2. customprepared

Sources & evidence

ORD record
ord-cd1c6a6fcae240f3a166d0550446c94a
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

Loading…