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

HRID 1618605Notes

Reaction equation

HRID 1618605 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][CH:23]=[C:24]([Cl:27])[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](=[CH:22][CH:23]=[C:24]([Cl:27])[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 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)HCID 609949634,6-Dichloro-2,3-dimethylquinoline

Product 1

HCID 672847956-Bromo-1-(6-chloro-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-2,3-dimethylquinoline (0.2783 g, 1.23 mmol) to give 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 8.03 (1H, d, J=9.0 Hz), 7.71 (1H, dd, J=8.9, 2.3 Hz), 7.65 (1H, d, J=2.2 Hz), 7.22 (1H, d, J=7.8 Hz), 6.83 (1H, dd, J=7.8, 1.5 Hz), 5.94 (1H, d, J=1.5 Hz), 4.04 (1H, d, J=9.8 Hz), 3.80-3.93 (3H, m), 3.39-3.54 (2H, m), 2.68 (3H, s), 2.22 (3H, s), 1.94-2.06 (2H, m), 1.85 (1H, d, J=13.4 Hz), 1.73 (1H, dd, J=13.4, 1.5 Hz); Mass Spectrum (ESI) m/e=457.1 [M+1 (79Br)] and 459.1 [M+1 (81Br)].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7be915d10a1d41e994fa19e0682df155
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…