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

HRID 1618599Notes

Reaction equation

HRID 1618599 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=3)[N:14]=[C:13]([CH3:22])[C:12]=2[CH3:23])=[C:4]([O:24][CH3:25])[CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][NH:37][CH:38]=2)O1>>[Cl:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:22])[C:12]([CH3:23])=[C:11]2[N:8]1[C:9]2[C:5](=[C:4]([O:24][CH3:25])[CH:3]=[C:2]([C:34]3[CH:35]=[N:36][NH:37][CH:38]=3)[CH:10]=2)[CH:6]=[CH:7]1

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 672850594-(6-bromo-4-methoxy-1H-indol-1-yl)-6-chloro-2,3-dimethylquinoline

Product 1

HCID 509403316-chloro-4-(4-methoxy-6-(1H-pyrazol-4-yl)-1H-indol-1-yl)-2,3-dimethylquinoline

Procedure

Prepared according to procedure W using 4-(6-bromo-4-methoxy-1H-indol-1-yl)-6-chloro-2,3-dimethylquinoline (0.4 g, 0.962 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.3734 g, 1.92 mmol) to give 6-chloro-4-(4-methoxy-6-(1H-pyrazol-4-yl)-1H-indol-1-yl)-2,3-dimethylquinoline as a white solid: 1H NMR (500 MHz, DMSO-d6) δ ppm 8.09 (2H, d, J=9.0 Hz), 7.81 (1H, s), 7.73 (1H, dd, J=8.9, 2.3 Hz), 7.39 (1H, d, J=3.2 Hz), 6.90-6.94 (2H, m), 6.80 (1H, dd, J=3.2, 0.5 Hz), 6.63 (1H, s), 4.00-4.06 (4H, m), 2.77 (3H, s), 2.06 (3H, s); Mass Spectrum (ESI) m/e=403.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-531d22125b544df5b54c467ab5cc103c
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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