Triethylamine → N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide

HRID 558142노트

반응식

HRID 558142 반응식
[F:1][CH:2]([F:6])[C:3](O)=[O:4].[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH:15]([NH2:17])[CH3:16].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH:15]([NH:17][C:3](=[O:4])[CH:2]([F:6])[F:1])[CH3:16]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 570869192-Bromo-4-fluoro-α-methylbenzenemethanamine

생성물 1

HCID 57445093N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide수율 66.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Add difluoroacetic acid (777 mg, 8.1 mmol) to a mixture of 1-(2-bromo-4-fluorophenyl)ethanamine (1.18 g, 5.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.55 g, 8.1 mmol), 1-hydroxybenzotriazole hydrate (1.24 g, 8.1 mmol), and triethylamine (2.26 mL, 16.2 mmol) in DCM (20 mL) at 0° C. Stir the mixture at RT overnight. Dilute the mixture with DCM, wash with water and aqueous saturated sodium chloride. Separate the organic layer and dry over sodium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography [5% to 50% ethyl acetate in hexanes] to give the title compound (1.06 g, 44%). MS (ES) m/z 296 [M+1]+.

후처리

  1. washwash with water and aqueous saturated sodium chloride
  2. customSeparate the organic layer
  3. dry with materialdry over sodium sulfate
  4. filtrationFilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by column chromatography [5% to 50% ethyl acetate in hexanes]

출처 및 근거

ORD 기록
ord-f65d95b124214c7fbf1caddf6f6481ca
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063035B2

반응 노트

불러오는 중…