Hydrochloric Acid → 6-(4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one

HRID 1618551Notes

Reaction equation

HRID 1618551 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:5]2=[N:6][CH:7]=1.Cl.O1CCOCC1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=2)[N:24]=[C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38]C)[N:33]=2)[C:22]=1[CH3:40]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([C:21]3[C:30]4[C:25](=[CH:26][C:27]([F:31])=[CH:28][CH:29]=4)[N:24]=[C:23]([C:32]4[NH:33][C:34](=[O:38])[CH:35]=[CH:36][CH:37]=4)[C:22]=3[CH3:40])[CH2:9][C:8]([CH3:12])([CH3:11])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 672849816-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridineHCID 672853724-Chloro-7-fluoro-2-(6-methoxypyridin-2-yl)-3-methylquinoline

Product 1

HCID 672846726-(4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Prepared according to procedure L using 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine (108 mg, 0.48 mmol) (described herein), 4.0M hydrochloric acid in 1,4-dioxane (100 μL, 0.40 mmol), 4-chloro-7-fluoro-2-(6-methoxypyridin-2-yl)-3-methylquinoline (120 mg, 0.40 mmol) (described herein), and NMP (660 μL). The reaction mixture was stirred and heated in a microwave at 150° C. for 180 min. Purification afforded 6-(4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one as a yellow solid. Mass Spectrum (ESI) m/e=479 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-a9fd1f8a30dc4d71ac7d9547261b7afa
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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