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Triethylamine → Ethyl(E)-3-[6-[(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazin-8-yl)-(tert-butyldimethylsiloxy)methyl]pyridin-2-yl]-2-propenoate

HRID 1059409
ノート
印刷プレビュー

反応式

HRID 1059409 の反応式
Br[C:2]1[N:7]=[C:6]([CH:8]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:9]2[CH:10]=[CH:11][C:12]3[S:17][C:16]4[N:18]=[CH:19][CH:20]=[N:21][C:15]=4[N:14]([CH2:22][O:23][CH3:24])[C:13]=3[CH:25]=2)[CH:5]=[CH:4][CH:3]=1.[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH3:24][O:23][CH2:22][N:14]1[C:13]2[CH:25]=[C:9]([CH:8]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:6]3[N:7]=[C:2](/[CH:36]=[CH:35]/[C:34]([O:38][CH2:39][CH3:40])=[O:37])[CH:3]=[CH:4][CH:5]=3)[CH:10]=[CH:11][C:12]=2[S:17][C:16]2[N:18]=[CH:19][CH:20]=[N:21][C:15]1=2
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

9

反応物 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 186705248-[(6-Bromopyridin-2-yl)-(tert-butyldimethylsiloxy)methyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

生成物 1

HCID 18670598Ethyl(E)-3-[6-[(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazin-8-yl)-(tert-butyldimethylsiloxy)methyl]pyridin-2-yl]-2-propenoate

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a solution of 0.72 g of 8-[(6-bromopyridin-2-yl)-(tert-butyldimethylsiloxy)methyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (8 ml) were added 0.17 ml of ethyl acrylate, 0.22 ml of triethylamine, 12 mg of palladium (II) acetate and 33 mg of triphenylphosphine and the resulting mixture was heated to 90° C. for 30 hours. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The organic layer was extracted, washed successively with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (diluted with dichloromethane/ethyl acetate) to thereby give 540 mg of the title compound as a yellow oily substance.

後処理

  1. customwas brought back to room temperature
  2. extractionThe organic layer was extracted
  3. washwashed successively with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (diluted with dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-1923915fbb0d43578a85e02b2137e2be
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06518423B1

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