4-Chloro-2,3,8-trimethylquinoline → 6-Bromo-1-(2,3,8-trimethylquinolin-4-yl)-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

HRID 1618609Notes

Reaction equation

HRID 1618609 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](=[C:22]([CH3:27])[CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH3:28])[C:18]=1[CH3:29]>>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:17]3[C:26]4[C:21](=[C:22]([CH3:27])[CH:23]=[CH:24][CH:25]=4)[N:20]=[C:19]([CH3:28])[C:18]=3[CH3:29])[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 160906094-Chloro-2,3,8-trimethylquinolineHCID 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)

Product 1

HCID 672853426-Bromo-1-(2,3,8-trimethylquinolin-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] (0.5 g, 1.86 mmol) and 4-chloro-2,3,8-trimethylquinoline (0.4219 g, 2.05 mmol) to give 6-bromo-1-(2,3,8-trimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (2H, dd, J=17.2, 7.4 Hz), 7.37 (1H, dd, J=8.2, 7.0 Hz), 7.20 (1H, d, J=7.8 Hz), 6.78 (1H, dd, J=7.8, 1.6 Hz), 5.82 (1H, d, J=2.0 Hz), 3.83-4.00 (4H, m), 3.39-3.54 (2H, m), 2.73 (3H, s), 2.71 (3H, s), 2.24 (3H, s), 1.92-2.10 (2H, m), 1.66-1.90 (2H, m); Mass Spectrum (ESI) m/e=437.0 [M+1 (79Br)] and 439.1 [M+1 (81Br)].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-efd5983ae9c6420ea2fcc44f9aaa6229
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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