Triethylamine → N-[1-(3-Pentafluoroethyl-phenyl)-vinyl]-acetamide

HRID 1098749

반응식

HRID 1098749 반응식
[F:1][C:2]([F:21])([C:7]1[CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=[CH:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4].[CH:22]([NH:24][C:25](=[O:27])[CH3:26])=[CH2:23].C(N(CC)CC)C.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]([F:21])([C:7]1[CH:8]=[C:9]([C:22]([NH:24][C:25](=[O:27])[CH3:26])=[CH2:23])[CH:10]=[CH:11][CH:12]=1)[C:3]([F:6])([F:5])[F:4]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 78875N-VinylacetamideHCID 12091099Phosphine, (1-methylethylidene)bis[diphenyl-HCID 59506217Trifluoro-methanesulfonic acid 3-pentafluoroethyl-phenyl ester

생성물 1

HCID 59506293N-[1-(3-Pentafluoroethyl-phenyl)-vinyl]-acetamide

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a solution of the crude product of step 1 (0.75 g, 2.2 mmol) in DMF (10 ml) was added N-vinylacetamide (0.37 g, 4.36 mmol), triethylamine (243 mg, 0.33 ml, 2.40 mmol), palladium acetate (20 mg, 4 mol %) and bis(diphenylphosphino)propane (40 mg, 0.1 mmol). The reaction mixture was heated for 30 min at 130° C. using microwaves. The red solution was diluted and washed with hydrochloric acid (1M, 2×15 ml) and sodium hydrogen carbonate (saturated, 20 ml). The organic phase was dried over sodium sulphate and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane (2:1) gave the desired product.

후처리

  1. additionThe red solution was diluted
  2. washwashed with hydrochloric acid (1M, 2×15 ml) and sodium hydrogen carbonate (saturated, 20 ml)
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customPurification of the crude product by silica gel chromatography

출처 및 근거

ORD 기록
ord-952ca0b47f1a49ef9fa38068bfe476a6
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143242B2

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