Sodium hydride → 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

HRID 1618560Notes

Reaction equation

HRID 1618560 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3]=1[CH3:19].[Br:20][C:21]1[CH:22]=[C:23]2[NH:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:24]2=[N:25][CH:26]=1.[H-].[Na+]>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]2[N:29]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][C:10]=4[F:12])[N:5]=[C:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)[C:3]=3[CH3:19])[CH2:28][C:27]([CH3:31])([CH3:30])[C:24]2=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 596312094-Chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 672849816-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 672851004-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Prepared according to procedure M using 4-chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (86 mg, 0.32 mmol) (described herein), 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine (86 mg, 0.38 mmol) (described herein), and sodium hydride (25 mg, 0.63 mmol) in DMF (10 mL). Reaction was heated at 60° C. for 18 h, affording 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-1-yl)-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline as an orange solid. Mass Spectrum (ESI) m/e=463 (M+1).

Workup

  1. customPrepared
  2. customReaction

Sources & evidence

ORD record
ord-daa198e4481546efa717a4c91ba294c2
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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