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Sodium triacetoxyborohydride → 7-(2-hydroxyethyl)-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706636
ノート
印刷プレビュー

反応式

HRID 706636 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([CH2:23][CH:24]=[O:25])=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[N:4]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=2)[N:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCO>[OH:25][CH2:24][CH2:23][C:21]1[CH:20]=[CH:19][N:18]2[C:14]([C:12]([NH:11][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([CH3:1])=[N:3][N:4]4[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=3)=[O:13])=[CH:15][N:16]=[C:17]2[CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 5049666Sodium triacetoxyborohydrideHCID 86699334N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 573874117-(2-hydroxyethyl)-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 76.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-oxoethyl)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.011 mmol) in 0.5 mL absolute EtOH was treated at ambient temperature with 3 equivalents of sodium triacetoxyborohydride. The reaction mixture was stirred overnight at ambient temperature, after which another 10 equivalents reducing agent were added. Stirring was continued until starting material was consumed. The reaction was quenched with excess saturated aqueous sodium bicarbonate solution, and extracted with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated. The crude product was subjected to preparative thin-layer chromatography on silica with 5% MeOH/DCM as eluent to afford 3.7 mg of product as a white solid. MS (ES+APCI) m/z=441 (M+H) detected.

後処理

  1. additionwere added
  2. stirringStirring
  3. customwas consumed
  4. customThe reaction was quenched with excess saturated aqueous sodium bicarbonate solution
  5. extractionextracted with DCM and EtOAc
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-6cf347216ad146d6889060b220265fd1
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174981B2

反応ノート

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