1-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-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-piperidinone

HRID 1618681Notes

Reaction equation

HRID 1618681 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[CH2:19][CH2:18][CH2:17][CH2:16][C:15]2=[O:20])[C:3]=1[CH3:21].[CH3:22][C:23]1([CH3:38])[C:27]2=[N:28][CH:29]=[C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:31]=[C:26]2[NH:25][CH2:24]1>C1(C)C=CC=CC=1>[CH3:22][C:23]1([CH3:38])[C:27]2=[N:28][CH:29]=[C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:31]=[C:26]2[N:25]([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[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3=[O:20])[C:3]=2[CH3:21])[CH2:24]1

Participants

4

Reactant 2

HCID 596310611-(4-Bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-oneHCID 672844994-(3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-morpholine

Product 1

HCID 509394671-(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-piperidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure Y using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one (53.0 mg, 0.150 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-piperidinone. 1H NMR (400 MHz, chloroform-d) δ ppm 7.60-7.69 (1H, m), 7.50-7.59 (1H, m), 6.89-7.09 (1H, m), 6.06 (1H, d, J=2.0 Hz), 4.21-4.36 (1H, m), 4.00 (1H, d, J=8.8 Hz), 3.68-3.92 (4H, m), 3.50-3.68 (2H, m), 3.11 (3H, dd, J=5.9, 3.7 Hz), 2.92-3.06 (2H, m), 2.52-2.70 (2H, m), 1.94-2.18 (6H, m), 1.49-1.64 (6H, m). Mass Spectrum (ESI) m/e=508.3 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c2cd44df6b584137abb7f8f198e5d93f
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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