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Dimethylformamide → Ethyl 8-(benzyloxy)-6-cyano-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

HRID 494106
ノート
印刷プレビュー

反応式

HRID 494106 の反応式
[CH2:1]([O:8][C:9]1[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:11](Br)[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:14](=[O:26])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:52][N:53](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:11]([C:52]#[N:53])[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:14](=[O:26])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 68864116Ethyl 8-(benzyloxy)-6-bromo-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

生成物 1

HCID 68864512Ethyl 8-(benzyloxy)-6-cyano-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

試薬・触媒・溶媒 2

HCID 11186
Zinc cyanide (Zn(CN)2)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

A solution of ethyl 8-(benzyloxy)-6-bromo-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate (1.40 g, 2.79 mmol; Example 1, Step 7), zinc cyanide (0.26 g, 2.23 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.51 g, 0.56 mmol), triphenylphosphine (0.15 g, 0.56 mmol) in DMF (4.5 mL) was purged with nitrogen for 5 minutes. The reaction mixture was heated at 100° C. overnight and concentrated under vacuum. The reaction mixture was partitioned between dichloromethane and brine. The organic extract was dried over sodium sulfate, filtered and concentrated. The residue was subjected to column chromatography on silica gel eluted with 0-10% methanol in chloroform gradient to provide titled product.

後処理

  1. concentrationconcentrated under vacuum
  2. customThe reaction mixture was partitioned between dichloromethane and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluted with 0-10% methanol in chloroform gradient

出典と根拠

ORDレコード
ord-fd3ea4ca3a4646e4b1c6b6078d159930
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538112B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート