1-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one → 1-(4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-quinolinyl)-2-pyrrolidinone

HRID 1618696Notes

Reaction equation

HRID 1618696 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[C:3]=1[CH3:20].[CH3:21][C:22]1([CH3:37])[C:26]2=[N:27][CH:28]=[C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:30]=[C:25]2[NH:24][CH2:23]1>C1(C)C=CC=CC=1>[CH3:21][C:22]1([CH3:37])[C:26]2=[N:27][CH:28]=[C:29]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:30]=[C:25]2[N:24]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=3[F:12])[N:5]=[C:4]([N:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[O:19])[C:3]=2[CH3:20])[CH2:23]1

Participants

4

Reactant 2

HCID 596310731-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-oneHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

Product 1

HCID 672852411-(4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-quinolinyl)-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyrrolidin-2-one (55.0 mg, 0.160 mmol) and 4-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)morpholine in toluene to give 1-(4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-2-quinolinyl)-2-pyrrolidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.67 (1H, d, J=2.3 Hz), 7.54 (1H, ddd, J=9.2, 2.4, 1.3 Hz), 7.05 (1H, ddd, J=12.3, 8.6, 2.5 Hz), 6.14 (1H, d, J=2.2 Hz), 4.26-4.41 (1H, m), 4.07-4.12 (1H, m), 4.04 (1H, d, J=9.2 Hz), 3.69-3.83 (5H, m), 3.12-3.18 (4H, m), 2.63-2.71 (2H, m), 2.27-2.40 (2H, m), 2.18 (3H, s), 1.70 (3H, s), 1.67 (3H, s). Mass Spectrum (ESI) m/e=494.2 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a25ee3e8b4e24c6eb4cd8d0d1d8f437a
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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