Pentapotassium Triphosphate → N-[6-(Azetidin-1-yl)pyridin-3-yl]-5-tert-butyl(dimethyl)silyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1948799Notes

Reaction equation

HRID 1948799 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.[C:32]([SiH:36]([CH3:38])[CH3:37])([CH3:35])([CH3:34])[CH3:33].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]>CN1CCCC1=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]([CH:22]=3)=[CH:20][C:19]([Si:36]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:38])[CH3:37])=[CH:18][CH:17]=4)=[O:13])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 61695Pentapotassium TriphosphateHCID 5072427tert-ButyldimethylsilaneHCID 66850586HCID 66850586, compound

Product 1

HCID 66850262N-[6-(Azetidin-1-yl)pyridin-3-yl]-5-tert-butyl(dimethyl)silyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 17.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound No. 18 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 108 mg (0.93 mmol) of tert-butyldimethylsilane 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). 28 mg of the expected product are obtained.

Workup

  1. custom18 was prepared
  2. customprepared

Sources & evidence

ORD record
ord-5605e4e75d364451b3dbf4645c490b24
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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