Sodium Carbonate → N-Quinolin-7-yl-6-(4-trifluoromethylphenyl)-nicotinamide

HRID 494264

反応式

HRID 494264 の反応式
Cl[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCOC(C)=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>[N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:19]=[CH:20][C:2]([C:26]4[CH:27]=[CH:28][C:23]([C:22]([F:33])([F:32])[F:21])=[CH:24][CH:25]=4)=[N:3][CH:4]=3)[CH:18]=2)[CH:13]=[CH:14][CH:15]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 445789876-Chloro-N-quinolin-7-yl-nicotinamide

生成物 1

HCID 44578937N-Quinolin-7-yl-6-(4-trifluoromethylphenyl)-nicotinamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-chloro-N-quinolin-7-yl-nicotinamide (D70) (40 mg, 0.14 mmol) in DME (0.9 ml) under an argon atmosphere was added 4-trifluoromethylphenylboronic acid (33 mg, 0.17 mmol), 2M sodium carbonate solution (0.17 ml) and tetrakis(triphenylphosphine)palladium (0) (8 mg, 0.007 mmol). The reaction was heated at reflux until complete by tlc, then cooled to room temperature and diluted with EtOAc and dried over MgSO4. The solvent was removed in vacuo and the resultant crude product was purified by SPE column chromatography. Elution with 75% EtOAc in 40-60° C. petroleum ether gave the title compound as an off-white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.31 (dd, 1H), 8.83 (dd, 1H), 8.46 (dd, 1H), 8.39 (dd, 1H), 8.20 (m, 3H), 8.07 (d, 1H), 7.94 (dd, 1H), 7.89 (d, 1H), 7.79 (d, 2H), 7.40 (dd, 1H).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux until complete by tlc
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe resultant crude product was purified by SPE column chromatography
  6. washElution with 75% EtOAc in 40-60° C. petroleum ether

出典と根拠

ORDレコード
ord-3804f545fe4b4c91a07d363bb8bdb01c
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

関連ノート

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