Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline

HRID 1618484Notes

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][CH:25]=[CH:26][C:27]=2[F:29])[N:22]=[C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[C:20]=1[CH3:36].[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][CH:25]=[CH:26][C:27]=3[F:29])[N:22]=[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[C:20]=2[CH3:36])[CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

Prepared according to procedure M using 3,3-dimethyl-6-morpholinoindoline (348 mg, 1496 μmol), 4-chloro-5-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (340 mg, 1247 μmol) in DMF (12 mL), and sodium hydride (72 mg, 2992 μmol) and heating at 130° C. overnight. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.76 (1H, dd, J=3.5, 1.2 Hz), 8.02 (1H, d, J=8.2 Hz), 7.83-7.96 (2H, m), 7.60 (1H, td, J=8.1, 5.3 Hz), 7.40 (1H, ddd, J=7.0, 5.1, 2.0 Hz), 7.08-7.17 (1H, m), 7.04 (1H, d, J=8.2 Hz), 6.26 (1H, dd, J=8.0, 2.2 Hz), 5.50 (1H, d, J=2.3 Hz), 3.76-3.85 (1H, m), 3.60-3.76 (5H, m), 2.86-3.02 (4H, m), 2.42 (3H, s), 1.50 (3H, s), 1.44 (3H, s). Mass Spectrum (ESI) m/e=469 (M+1).

Workup

customPrepared
customAfter purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-5-fluoro-3-methyl-2-(2-pyridinyl)quinoline
customwas obtained as a yellow film

Sources & evidence

ORD record: ord-7150fce93a4349fba7f009d422b09950
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

Loading…