4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 1-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-pyridinyl)-1H-indole-4-carbonitrile

HRID 1618602Notes

Reaction equation

HRID 1618602 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:24]#[N:25])[C:5]2[CH:6]=[CH:7][N:8]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=4)[N:14]=[C:13]([CH3:22])[C:12]=3[CH3:23])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=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[CH:10]=[C:2]([C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH:3]=[C:4]([C:24]#[N:25])[C:5]=2[CH:6]=[CH:7]1

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 672853536-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-4-carbonitrile

Product 1

HCID 509402251-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-pyridinyl)-1H-indole-4-carbonitrile

Procedure

Prepared according to procedure W using 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-4-carbonitrile (0.2 g, 0.243 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.06 g, 0.292 mmol) to give 1-(6-chloro-2,3-dimethyl-4-quinolinyl)-6-(4-pyridinyl)-1H-indole-4-carbonitrile as a: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.55 (2H, d, J=5.9 Hz), 8.22 (1H, d, J=1.2 Hz), 8.12 (1H, d, J=9.0 Hz), 8.01 (1H, d, J=3.1 Hz), 7.70-7.79 (4H, m), 7.11 (1H, d, J=3.1 Hz), 6.91 (1H, d, J=2.3 Hz), 2.78 (3H, s), 2.02 (3H, s); Mass Spectrum (ESI) m/e=409.1 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c3e102617b084e20bae4c76d66faad5f
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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