HCID 89443836, 화합물 → HCID 89443808, 화합물

HRID 1771716노트

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HRID 1771716 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:20]=1)[C:6]([NH:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=1[F:17])=O)#[N:2]>C1COCC1>[F:17][C:10]1[C:11]([OH:16])=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[NH:8][CH2:6][C:5]1[CH:4]=[C:3]([CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:18]=1)[C:1]#[N:2]

참가 물질

3

반응물 1

HCID 89443836HCID 89443836, 화합물

생성물 1

HCID 89443808HCID 89443808, 화합물수율 29,267.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

To a solution of 3-Cyano-N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)benzamide (500 mg, 2.7 mmol, 1.0 eq) in THF (30 mL) at 0° C. was added a solution of BH3 (1M in THF, 10.8 mL, 10.8 mmol, 4.0 eq) dropwise. The reaction was then heated at 50° C. for 6 h. The reaction was cooled to room temperature and quenched by addition of aqueous NH4Cl. The aqueous layer was extracted with EtOAc and the combined organic extracts dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 7:1) to give the title compound as white solid (280 g, 58%).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by addition of aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether:EtOAc, 7:1)

출처 및 근거

ORD 기록
ord-053f1ee0463045d29516fbcc35fca811
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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