4-Fluorophenylboronic acid → HCID 18444638, 화합물

HRID 2266837노트

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HRID 2266837 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-d6b8118aa78644309bf59287660af75c
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858644B2

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