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

HRID 1618494Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[C:3]=1[CH3:21].[CH3:22][C:23]1([CH3:38])[C:31]2[C:26](=[CH:27][C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:29][CH:30]=2)[NH:25][CH2:24]1.[H-].[Na+]>CN(C=O)C>[CH3:22][C:23]1([CH3:38])[C:31]2[C:26](=[CH:27][C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:29][CH:30]=2)[N:25]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[C:3]=2[CH3:21])[CH2:24]1

Participants

Conditions

Temperature: 130 °C

Procedure

Prepared according to procedure M using 3-(4-chloro-7-fluoro-3-methylquinolin-2-yl)benzonitrile (220 mg, 0.74 mmol), 3,3-dimethyl-6-morpholinoindoline (189 mg, 0.816 mmol), sodium hydride (36 mg, 1.48 mmol) in DMF (2.0 mL) and heating at 130° C. overnight. After purification 3-(4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-quinolinyl)benzonitrile was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 7.94-7.98 (1H, m), 7.85-7.91 (2H, m), 7.75-7.82 (2H, m), 7.64 (1H, t, J=7.8 Hz), 7.23-7.31 (1H, m), 7.10 (1H, d, J=8.2 Hz), 6.35 (1H, dd, J=8.2, 2.3 Hz), 5.55-5.63 (1H, m), 3.68-3.79 (6H, m), 2.91-3.04 (4H, m), 2.28 (3H, s), 1.50-1.54 (3H, m), 1.47 (3H, s). Mass Spectrum (ESI) m/e=493 (M+1).

Workup

customPrepared
customAfter purification 3-(4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-7-fluoro-3-methyl-2-quinolinyl)benzonitrile
customwas obtained as a yellow film

Sources & evidence

ORD record: ord-1f74661024254579a634573fddb56c85
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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