Potassium Carbonate → 1-[4'-(5-fluoro-3,3-dimethyl-2,3-dihydro-indole-1-carbonyl)-6'-methoxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 74671Notes

Reaction equation

HRID 74671 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.Cl[C:20]1[CH:25]=[C:24]([C:26]([N:28]2[C:36]3[C:31](=[CH:32][C:33]([F:37])=[CH:34][CH:35]=3)[C:30]([CH3:39])([CH3:38])[CH2:29]2)=[O:27])[CH:23]=[C:22]([O:40][CH3:41])[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[F:37][C:33]1[CH:32]=[C:31]2[C:36](=[CH:35][CH:34]=1)[N:28]([C:26]([C:24]1[CH:23]=[C:22]([O:40][CH3:41])[N:21]=[C:20]([N:3]3[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]3)[CH:25]=1)=[O:27])[CH2:29][C:30]2([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 58386445(2-Chloro-6-methoxy-pyridin-4-yl)-(5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 426140891-[4'-(5-fluoro-3,3-dimethyl-2,3-dihydro-indole-1-carbonyl)-6'-methoxy-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.26 g (0.9 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one dihydrochloride, 0.30 g (0.9 mmol) (2-chloro-6-methoxy-pyridin-4-yl)-(5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-methanone and 0.37 g (2.7 mmol) potassium carbonate were stirred in 3 mL NMP for 12 h at 130° C. The reaction mixture was purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-97aa314fab5c4c16bf6ac3fe5d37471d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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