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

HRID 49718

反応式

HRID 49718 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6262f3f25e28483c9c0573b9c3afc165
出典データセット
uspto-grants-2004_03
特許番号
US06706738B2

関連ノート

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