Cesium carbonate → 5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester

HRID 33527

反応式

HRID 33527 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>CN(C)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>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:26][CH:25]=2)[CH:8]=[N:7][CH:6]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 27343864-(Trifluoromethoxy)phenylboronic acid

生成物 1

HCID 580025915-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester収率 54.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

81 mg (0.07 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 1.0 g (4.63 mmol) methyl-5-bromo-pyridine-3-carboxylate in 23 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 2.26 g (6.94 mmol) cesium carbonate and 1.05 g (5.09 mmol) of 4-(trifluoromethoxy)phenyl boronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 0.75 g (49%) of 5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. washwashed twice with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-35dac7309df84df983f033476176a726
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

関連ノート

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