6-Chloro-4-(6-iodo-3,3-dimethylindolin-1-yl)-2,3-dimethylquinoline → 6-chloro-4-(3,3-dimethyl-6-(4-pyridinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline

HRID 1618589Notes

Reaction equation

HRID 1618589 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH3:13])=[C:5]2[N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20](I)[CH:21]=2)[C:16]([CH3:25])([CH3:24])[CH2:15]1.OC(C(O)(C)C)(C)C.[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH3:13])=[C:5]2[N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:37]3[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=3)[CH:21]=2)[C:16]([CH3:25])([CH3:24])[CH2:15]1

Participants

3

Reactant 2

HCID 672846176-Chloro-4-(6-iodo-3,3-dimethylindolin-1-yl)-2,3-dimethylquinolineHCID 67285775Pyridine-4-boronic acid pinacol

Product 1

HCID 509404536-chloro-4-(3,3-dimethyl-6-(4-pyridinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline

Procedure

Prepared according to procedure W using 6-chloro-4-(6-iodo-3,3-dimethylindolin-1-yl)-2,3-dimethylquinoline (0.15 g, 0.32 mmol) and pyridine-4-boronic acid pinacol (0.1329 g, 0.65 mmol) to give 6-chloro-4-(3,3-dimethyl-6-(4-pyridinyl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.53 (2H, d, J=4.3 Hz), 8.02 (1H, d, J=9.0 Hz), 7.82 (1H, d, J=2.3 Hz), 7.60 (1H, dd, J=9.0, 2.3 Hz), 7.28-7.35 (3H, m), 7.04 (1H, dd, J=7.6, 1.4 Hz), 6.12 (1H, d, J=1.2 Hz), 3.63-3.88 (2H, m), 2.75 (3H, s), 2.27 (3H, s), 1.60 (3H, s), 1.54 (3H, s); Mass Spectrum (ESI) m/e=414.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9b24e598cc9448ebb0a3dc2af8264657
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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