Sodium Carbonate → 8-Methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

HRID 216762ノート

反応式

HRID 216762 の反応式
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CC#N.O.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>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([F:27])([F:26])[F:15])[C:11]([CH:12]=[O:13])=[CH:10]2

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 27343872-(Trifluoromethyl)benzeneboronic acid

生成物 1

HCID 575561608-Methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Prepared according to Procedure A using 2-chloro-8-methylquinoline-3-carbaldehyde (2.0 g, 9.73 mmol), 2-(trifluoromethyl)phenylboronic acid (2.032 g, 10.7 mmol, 1.1 eq), tetrakis(triphenylphosphine)palladium (562 mg, 5% mmol), and sodium carbonate (5.15 g, 48.6 mol, 5 eq) in MeCN (75 mL) and water (25 mL). After purification, 8-methyl-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde was obtained as a white solid. 1H NMR (DMSO-d6) δ ppm 9.93 (1H, s), 9.04 (1H, s), 8.13 (1H, d, J=8.1 Hz), 7.93 (1H, d, J=7.3 Hz), 7.85 (1H, d, J=7.1 Hz), 7.72-7.82 (2H, m), 7.64-7.71 (1H, m), 7.59 (1H, d, J=7.3 Hz), 2.67 (3H, s). Mass Spectrum (ESI) m/e=316.1 (M+1).

後処理

  1. customPrepared
  2. customAfter purification

出典と根拠

ORDレコード
ord-90f81b3f6d6d400da87ba9379ae9db1d
出典データセット
uspto-grants-2012_06
特許番号
US08193199B2

反応ノート

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