Triethylamine → Ethyl 3-(6-acetylamino-pyrid-3-yl)-but-2-enoate

HRID 49718

반응식

HRID 49718 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.[C:12]([O:17][CH2:18][CH3:19])(=[O:16])/[CH:13]=[CH:14]/[CH3:15].C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([C:14]([CH3:15])=[CH:13][C:12]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 2930972-Acetamido-5-bromopyridineHCID 429065Ethyl trans-crotonate

생성물 1

HCID 69687042Ethyl 3-(6-acetylamino-pyrid-3-yl)-but-2-enoate

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of N-(5-bromopyrid-2-yl)acetamide (31.4 g, Reference Example 23), ethyl crotonate (37.0 mL), triethylamine (33 mL), tetrakis(tri-o-tolylphosphine)palladium(0) and tetrabutylammonium bromide (9.36 g) in dimethylformamide (250 mL) was heated at 100° C. under an argon atmosphere for 48 hours. The reaction mixture was cooled and then evaporated. The residue was partitioned between ethyl acetate and water and the organic phase was washed with brine, then dried over magnesium sulphate and then evaporated. The resulting light brown solid was subjected to flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (7:3, v/v) to give the title compound (27.3 g) as a pale yellow solid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. additionThe resulting light brown solid was subjected to flash chromatography on silica eluting with a mixture of pentane and ethyl acetate (7:3

출처 및 근거

ORD 기록
ord-6262f3f25e28483c9c0573b9c3afc165
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706738B2

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