Sodium Bicarbonate → HCID 89443836, 화합물

HRID 1771715노트

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HRID 1771715 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([OH:8])=O)#[N:2].[NH2:19][C:20]1[C:21]([F:28])=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[F:26].C([O-])(O)=O.[Na+]>O=S(Cl)Cl.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([NH:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([OH:27])[C:21]=1[F:28])=[O:8])#[N:2]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 227559833-Amino-2,4-difluorophenolHCID 89443880HCID 89443880, 화합물

생성물 1

HCID 89443836HCID 89443836, 화합물수율 67.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 24386Thionyl Chloride용매

실험 절차

3-Cyano-5-(3-fluorophenyl)benzoic acid (500 mg, 2.1 mmol, 1 eq) was dissolved in SOCl2 (15 mL) and heated at reflux overnight. The excess SOCl2 was removed under reduced pressure and the residue that remained dissolved in THF (10 mL) and added dropwise to a mixture of 3-amino-2,4-difluorophenol (280 mg, 2 mmol, 0.95 eq) and NaHCO3 (880 mg, 10.5 mmol, 5 eq) in THF (40 mL). The reaction was stirred at room temperature for 3 h, then filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 10:1) to give the title compound as a white solid (500 mg, 64%).

후처리

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe excess SOCl2 was removed under reduced pressure
  4. dissolutionthe residue that remained dissolved in THF (10 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 10:1)

출처 및 근거

ORD 기록
ord-225847c53064427c885b0b44ca8d4496
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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