4-Fluorophenylboronic acid → HCID 18444638, 화합물

HRID 460086노트

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HRID 460086 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][O:20][C:19]=2[CH3:23])=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:22]=[CH:21][O:20][C:19]=3[CH3:23])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 2856454-Fluorophenylboronic acidHCID 517044Potassium AcetateHCID 18444641HCID 18444641, 화합물

생성물 1

HCID 18444638HCID 18444638, 화합물수율 44.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

A mixture of (4-fluoro-phenyl)-boronic acid (300 mg, 2.1 mmoles), 3-(4-iodophenoxymethyl)-2-methyl-furan (123) (500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed, treated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg) and the mixture was agitated at 95° C. for 12 hours under an argon atmosphere. The mixture was concentrated in vacuo, partitioned between water (100 ml) and diethyl ether (200 ml). The aqueous phase was re-extracted with diethyl ether, and the combined etheral phases were dried and evaporated. The residue was purified by flash chromatography, using diethyl ether as eluent, to afford compound 124(200 mg) as a solid. This material was used directly.

후처리

  1. customwas degassed
  2. additiontreated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg)
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between water (100 ml) and diethyl ether (200 ml)
  5. extractionThe aqueous phase was re-extracted with diethyl ether
  6. customthe combined etheral phases were dried
  7. customevaporated
  8. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-098435adcb8f4df793aa38a91638a42e
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196089B2

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