Toluene → 1-(5,7-difluoro-3-methyl-4-(6-(4-morpholinyl)-2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)-2-quinolinyl)-2(1H)-pyridinone

HRID 1618707Notes

Reaction equation

HRID 1618707 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[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=[O:20])[C:3]=1[CH3:21].[O:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]3[NH:36][CH2:35][C:34]4([CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[C:31]3=N[CH:33]=2)[CH2:24][CH2:23]1.[C:42]1(C)C=CC=CC=1>>[F:12][C:10]1[CH:9]=[C:8]([F:13])[CH:7]=[C:6]2[C:11]=1[C:2]([N:36]1[C:30]3[C:31](=[CH:42][CH:33]=[C:28]([N:25]4[CH2:24][CH2:23][O:22][CH2:27][CH2:26]4)[CH:29]=3)[C:34]3([CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:35]1)=[C:3]([CH3:21])[C:4]([N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=[O:20])=[N:5]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 596311391-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2(1H)-oneHCID 672847056'-Morpholino-1',2,2',3,5,6-hexahydrospiro[pyran-4,3'-pyrrolo[3,2-b]pyridine]

Product 1

HCID 672849791-(5,7-difluoro-3-methyl-4-(6-(4-morpholinyl)-2',3',5',6'-tetrahydrospiro[indole-3,4'-pyran]-1(2H)-yl)-2-quinolinyl)-2(1H)-pyridinone

Procedure

Prepared according to procedure Y using 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2(1H)-one (35.0 mg, 0.100 mmol) and 6′-morpholino-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridine] in toluene to give 1-(5,7-difluoro-3-methyl-4-(6-(4-morpholinyl)-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-pyran]-1(2H)-yl)-2-quinolinyl)-2(1H)-pyridinone. 1H NMR (400 MHz, chloroform-d) δ ppm 8.41-8.47 (1H, m), 7.94-8.01 (1H, m), 7.74 (1H, d, J=2.3 Hz), 7.35 (1H, ddd, J=7.4, 5.0, 0.9 Hz), 7.27-7.32 (2H, m), 6.94 (1H, ddd, J=12.5, 8.6, 2.5 Hz), 6.03 (1H, d), 4.08-4.22 (3H, m), 4.01-4.06 (1H, m), 3.72-3.81 (4H, m), 3.37-3.57 (2H, m), 3.13 (4H, dd, J=6.2, 3.8 Hz), 2.52-2.69 (2H, m), 2.38 (3H, s), 1.72-1.93 (2H, m). Mass Spectrum (ESI) m/e=

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8da1e5f845674c02bd58cf1f32885d51
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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