4-Methylthiazole → 2'-Fluoro-4'-methyl-5-thiazol-5-yl-biphenyl-3-carboxylic acid methyl ester

HRID 506613ノート

反応式

HRID 506613 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[CH:8]=[C:9](I)[CH:10]=1)=[O:4].C[C:21]1[N:22]=[CH:23][S:24][CH:25]=1.CC(O[K])=O>CC(N(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]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[F:19])[CH:8]=[C:9]([C:25]2[S:24][CH:23]=[N:22][CH:21]=2)[CH:10]=1)=[O:4]

参加物

6

反応物 3

HCID 127484-MethylthiazoleHCID 59432554HCID 59432554、化合物HCID 178476685HCID 178476685、化合物

生成物 1

HCID 594325802'-Fluoro-4'-methyl-5-thiazol-5-yl-biphenyl-3-carboxylic acid methyl ester収率 68%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of 2′-fluoro-5-iodo-4′-methyl-biphenyl-3-carboxylic acid methyl ester (50 mg, 0.135 mmol) and 4-methylthiazole (57.4 mg, 0.675 mmol) in 10 ml of dimethylacetamide was added Pd(PPh3)4 (8 mg, 0.00675 mmol) and CH3COOK (20 mg, 0.2 mmol). The reaction mixture was heated to 100° C. and stirred overnight. After cooling down to room temperature, the mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexanes/EtOAc=1:5) to afford 30 mg (68%) of 2′-fluoro-4′-methyl-5-thiazol-5-yl-biphenyl-3-carboxylic acid methyl ester, MS (M+H)=328.

後処理

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (hexanes/EtOAc=1:5)

出典と根拠

ORDレコード
ord-d00a481a1541422caa85cec29afc0672
出典データセット
uspto-grants-2010_08
特許番号
US07786110B2

反応ノート

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