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

HRID 506613노트

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HRID 506613 반응식
[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]

참가 물질

6

반응물 3

HCID 127484-MethylthiazoleHCID 59432554HCID 59432554, 화합물HCID 178476685HCID 178476685, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d00a481a1541422caa85cec29afc0672
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786110B2

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