6-Bromo-1,2-dihydrospiro(indole-3,4'-oxane) → 6-Bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

HRID 1618607Notes

Reaction equation

HRID 1618607 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:28][CH3:29])=[C:24]([Cl:27])[CH:25]=2)[N:20]=[C:19]([CH3:30])[C:18]=1[CH3:31]>>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([O:28][CH3:29])=[C:24]([Cl:27])[CH:25]=4)[N:20]=[C:19]([CH3:30])[C:18]=3[CH3:31])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)HCID 672854564,6-Dichloro-7-methoxy-2,3-dimethylquinoline

Product 1

HCID 672850136-Bromo-1-(6-chloro-7-methoxy-2,3-dimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

Procedure

Prepared according to procedure M using 6-bromo-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran] (0.3 g, 1.12 mmol) and 4,6-dichloro-7-methoxy-2,3-dimethylquinoline (0.3152 g, 1.23 mmol) to give 6-bromo-1-(6-chloro-7-methoxy-2,3-dimethyl-4-quinolinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-pyran] as a: 1H NMR (500 MHz, DMSO-d6) δ ppm 7.65 (1H, s), 7.58 (1H, s), 7.21 (1H, d, J=8.1 Hz), 6.82 (1H, dd, J=7.8, 1.7 Hz), 5.90 (1H, d, J=1.7 Hz), 3.96-4.05 (4H, m), 3.82-3.92 (3H, m), 3.41-3.53 (2H, m), 2.66 (3H, s), 2.17 (3H, s), 1.95-2.06 (2H, m), 1.85 (1H, dd, J=13.4, 1.7 Hz), 1.72 (1H, dd, J=13.3, 1.8 Hz); Mass Spectrum (ESI) m/e=487.0 [M+1 (79Br)] and 489.1 [M+1 (81Br)].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2721e0a3cf524cd6a44583e59c0a886d
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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