Sodium hydride → 4-(3,3-Dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-8-fluoro-3-methyl-2-(2-pyridinyl)quinoline

HRID 1618498Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

Prepared according to procedure M using 4-chloro-8-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (235 mg, 0.86 mmol), 4-(3,3-dimethylindolin-6-yl)morpholine (200 mg, 0.86 mmol), sodium hydride (41 mg, 1.72 mmol) in DMF (2.0 mL) and heating at 130° C. for 4 h. After purification 4-(3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-indol-1-yl)-8-fluoro-3-methyl-2-(2-pyridinyl)quinoline was obtained as a yellow film. 1H NMR (400 MHz, chloroform-d) δ ppm 8.64-8.79 (1H, m), 7.87-7.98 (2H, m), 7.60-7.65 (1H, m), 7.32-7.42 (3H, m), 7.08 (1H, d, J=7.8 Hz), 6.31 (1H, dd, J=8.0, 2.2 Hz), 5.59 (1H, d, J=2.3 Hz), 3.63-3.83 (6H, m), 2.86-3.05 (4H, m), 2.43 (3H, s), 1.52 (3H, s), 1.47 (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)-8-fluoro-3-methyl-2-(2-pyridinyl)quinoline
customwas obtained as a yellow film

Sources & evidence

ORD record: ord-1b509d53a22f45ac8d10a799d8669847
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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