Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline

HRID 1618651Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1.Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[N:22]=[C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[F:36])[C:20]=1[CH3:37].[H-].[Na+]>CN(C=O)C>[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[N:4]([C:19]2[C:28]3[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=3)[N:22]=[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[C:20]=2[CH3:37])[CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

Prepared according to procedure M using 3,3-dimethyl-6-morpholinoindoline (110 mg, 473 μmol), 4-chloro-7-fluoro-2-(2-fluorophenyl)-3-methylquinoline (137 mg, 473 μmol) in DMF (2 mL), and sodium hydride (38 mg, 946 μmol) and heating at 130° C. for 7 h. After purification 4-(1-(7-fluorophenyl)-3-methylquinolin-4-yl)-3,3-dimethylindolin-4-yl)-3,3-dimethylindolin-6-yl)morpholine was obtained. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94-8.03 (1H, m), 7.85 (1H, dd, J=10.0, 2.5 Hz), 7.52-7.68 (3H, m), 7.34-7.45 (2H, m) 7.14 (1H, d, J=7.8 Hz), 6.50 (1H, br s), 5.80 (1H, br s), 3.88 (1H, d, J=9.4 Hz), 3.57-3.79 (5H, m), 2.99 (4H, br s), 2.052 (3H, s), 1.46 (3H, s), 1.38 (3H, s). Mass Spectrum (ESI) m/e=486 (M+1).

Workup

customPrepared
customAfter purification 4-(1-(7-fluorophenyl)-3-methylquinolin-4-yl)-3,3-dimethylindolin-4-yl)-3,3-dimethylindolin-6-yl)morpholine
customwas obtained

Sources & evidence

ORD record: ord-9961f5dce2ad481e87c02d8af76af609
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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