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

HRID 558142ノート

反応式

HRID 558142 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

  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]

出典と根拠

ORDレコード
ord-f65d95b124214c7fbf1caddf6f6481ca
出典データセット
uspto-grants-2011_11
特許番号
US08063035B2

反応ノート

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