6-Bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran] → HCID 67285125, compound

HRID 1618608Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]2[N:8]([C:16]3[C:25]4[C:20](=[CH:21][C:22]([O:27][CH3:28])=[C:23]([Cl:26])[CH:24]=4)[N:19]=[C:18]([CH3:29])[C:17]=3[CH3:30])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[C:31]([Cu])#[N:32]>CN(C=O)C>[Cl:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:27][CH3:28])[N:19]=[C:18]([CH3:29])[C:17]([CH3:30])=[C:16]2[N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([C:31]#[N:32])[CH:7]=2)[C:10]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:9]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (0.1 g, 0.205 mmol) and CuCN (0.0367 g, 0.41 mmol) in DMF (1 mL) was stirred at 150° C. After 48 h, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on a silica gel column using 0 to 100% gradient of EtOAc in hexane as eluent to give 1-(6-chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran]-6-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67 (1H, s), 7.59 (1H, s), 7.47 (1H, d, J=7.4 Hz), 7.12 (1H, dd, J=7.6, 1.4 Hz), 6.16 (1H, d, J=1.6 Hz), 4.10 (1H, d, J=9.8 Hz), 4.00 (3H, s), 3.82-3.94 (3H, m), 3.42-3.56 (2H, m), 2.66 (3H, s), 2.15 (3H, s), 1.98-2.11 (2H, m), 1.89 (1H, dd, J=13.7, 1.6 Hz), 1.74 (1H, dd, J=13.5, 1.0 Hz); Mass Spectrum (ESI) m/e=434.2 (M+1).

Workup

concentrationthe mixture was concentrated under reduced pressure
customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record: ord-4bf6e6f2c4bd4f34bdbccfdc997308ad
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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