Hexabutyldistannane → N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246566ノート

反応式

HRID 246566 の反応式
Br[C:2]1[N:7]=[C:6]2[C:8]([C:19]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9][N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:4][CH:3]=1.I[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[N:28]=1.CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC>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>[C:22]([NH:21][C:19]([C:8]1[C:6]2=[N:7][C:2]([C:27]3[C:35]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[N:29]([CH3:36])[N:28]=3)=[CH:3][N:4]=[C:5]2[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

参加物

6

反応物 3

HCID 6327815HexabutyldistannaneHCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridineHCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 71280190N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 68.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

To a solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (400 mg, 936 μmol) and 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (364 mg, 1.4 mmol) in DMF (8 mL) was added hexabutylditin (814 mg, 709 μL, 1.4 mmol) then the mixture was purged with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium (0) (54.1 mg, 46.8 μmol) was added and the reaction mixture was heated at 125° C. After 18 h the mixture was filtered through a pad of Celite to remove catalyst, then the filtrates were concentrated in vacuo and purified by chromatography (silica, 10-70% ethyl acetate in hexanes) to obtain N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (306 mg, 638 μmol, 68%) as an off-white powder. MS (M+H)+=480.

後処理

  1. customthe mixture was purged with nitrogen for 10 min
  2. filtrationAfter 18 h the mixture was filtered through a pad of Celite
  3. customto remove catalyst
  4. concentrationthe filtrates were concentrated in vacuo
  5. custompurified by chromatography (silica, 10-70% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-93f7f36ae35e483f8570aef10754e723
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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