Sodium Carbonate → 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-(1H-pyrazol-4-yl)-1H-indole-3-carbonitrile

HRID 1618638Notes

Reaction equation

HRID 1618638 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:24]#[N:25])=[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])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][NH:37][CH:38]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[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](=[CH:4][CH:3]=[C:2]([C:34]3[CH:35]=[N:36][NH:37][CH:38]=3)[CH:10]=2)[C:6]([C:24]#[N:25])=[CH:7]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 672845396-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile

Product 1

HCID 509399901-(6-chloro-2,3-dimethylquinolin-4-yl)-6-(1H-pyrazol-4-yl)-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile (0.2 g, 0.49 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.188 g, 0.97 mmol), and Pd(PPh3)4 (0.056 g, 0.049 mmol) in a 2M aqueous solution of Na2CO3 (1.5 mL) and DMF (5 mL) was stirred at 100° C. overnight. After this time the reaction mixture was allowed to cool to rt and poured into ice water. The resulting precipitate was filtered and purified via flash column chromatography to give 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-(1H-pyrazol-4-yl)-1H-indole-3-carbonitrile. 1H NMR (500 MHz, chloroform-d) δ ppm 8.02 (1H, d, J=9.0 Hz), 7.82 (1H, d, J=8.3 Hz), 7.64 (2H, m), 7.58 (2H, m), 7.49 (1H, dt, J=8.3, 0.7 Hz), 6.96 (1H, d, J=2.4 Hz), 6.82 (1H, s), 2.76 (3H, s), 2.01 (3H, s). Mass Spectrum (ESI) m/e=398 (M+1).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. custompurified via flash column chromatography

Sources & evidence

ORD record
ord-3b5833bb36374a9baed629a53352eea9
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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