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2-bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide → 2-[5-(2-tert-butylsilyloxypropan-2-yl)-1-methylindazol-3-yl]-N-propan-2-yl-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246319
ノート
印刷プレビュー

反応式

HRID 246319 の反応式
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13](Br)[N:14]=2)[N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[C:25]([SiH2:29][O:30][C:31]([CH3:56])([CH3:55])[C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH3:41])[N:36]=[C:35]2[Sn](CCCC)(CCCC)CCCC)([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([C:31]([CH3:56])([CH3:55])[O:30][SiH2:29][C:25]([CH3:27])([CH3:26])[CH3:28])[CH:33]=4)[N:37]([CH3:41])[N:36]=3)[N:14]=2)[N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=1)=[O:6])([CH3:3])[CH3:2]
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

6

反応物 2

HCID 585222792-bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideHCID 173502725Tert-butyl-[2-(1-methyl-3-tributylstannylindazol-5-yl)propan-2-yloxy]silane

生成物 1

HCID 1317312222-[5-(2-tert-butylsilyloxypropan-2-yl)-1-methylindazol-3-yl]-N-propan-2-yl-5-(2-trimethylsilylethoxymethyl)pyrrolo[2,3-b]pyrazine-7-carboxamide収率 95.8%

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

In a round-bottomed flask, 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide (300 mg, 0.73 mmol) and 5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-3-tributylstannanyl-1H-indazole (Example 273, 665 mg, 0.82 mmol) were dissolved in DMF (4.8 ml). The reaction mixture was evacuated and backfilled with argon then tetrakis(triphenylphosphine)palladium (0) (42 mg, 0.036 mmol) and copper (I) iodide (28 mg, 0.147 mmol) were added. The reaction mixture was stirred at 80° C. overnight then cooled to room temperature, quenched with water and diluted with petroleum ether. The resulting suspension was filtered and the solids washed with water, petroleum ether and a minimal amount of diethyl ether then dried under high vacuum to afford 426 mg (92%) of 2-[5-(tert-butyldimethyl-silanyloxymethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide as a brown powder.

後処理

  1. customThe reaction mixture was evacuated
  2. temperaturethen cooled to room temperature
  3. customquenched with water
  4. additiondiluted with petroleum ether
  5. filtrationThe resulting suspension was filtered
  6. washthe solids washed with water, petroleum ether
  7. dry with materiala minimal amount of diethyl ether then dried under high vacuum

出典と根拠

ORDレコード
ord-8bb4286975b4428ba12dc3a3d677ec75
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

読み込み中…

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