4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 6-chloro-4-(3,3-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline

HRID 1618590Notes

Reaction equation

HRID 1618590 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.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][NH:37][CH:38]=2)O1>>[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:34]3[CH:35]=[N:36][NH:37][CH:38]=3)[CH:21]=2)[C:16]([CH3:25])([CH3:24])[CH2:15]1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 672846176-Chloro-4-(6-iodo-3,3-dimethylindolin-1-yl)-2,3-dimethylquinoline

Product 1

HCID 509403356-chloro-4-(3,3-dimethyl-6-(1H-pyrazol-4-yl)-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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.084 g, 0.432 mmol) to give 6-chloro-4-(3,3-dimethyl-6-(1H-pyrazol-4-yl)-2,3-dihydro-1H-indol-1-yl)-2,3-dimethylquinoline as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 12.73 (1H, br. s.), 8.01 (1H, d, J=9.0 Hz), 7.91 (1H, br. s.), 7.75 (1H, d, J=2.4 Hz), 7.62-7.71 (2H, m), 7.19 (1H, d, J=7.6 Hz), 6.94 (1H, d, J=7.6 Hz), 6.07 (1H, s), 3.56-3.78 (2H, m), 2.68 (3H, s), 2.21 (3H, s), 1.48 (3H, s), 1.43 (3H, s); Mass Spectrum (ESI) m/e=403.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-40c3594d6ce34fe0ad2b6a8d867bb730
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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