Sodium borohydride → tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

HRID 1404611ノート

反応式

HRID 1404611 の反応式
[C:1]1(/[CH:7]=[N:8]/[N:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][N:21]([CH:23]5[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]5)[CH:22]=4)[CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.C([O-])(O)=O.[Na+]>[CH2:7]([NH:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]4)[CH:22]=3)[CH:16]=2)[CH:11]=[CH:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 58532304tert-butyl 4-[4-[1-[(E)-benzylideneamino]pyrrolo[3,2-b]pyridin-6-yl]pyrazol-1-yl]piperidine-1-carboxylate

生成物 1

HCID 67458095tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of tert-butyl 4-[4-(1-{[(E)-phenylmethylidene]amino}-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (200 mg, 0.43 mmol) in MeOH (10 mL) was treated with excess amount of NaBH4 under reflux. HPLC check indicates disappearance of the starting material. The mixture was diluted with aqueous NaHCO3, and extracted with ethylacetate. The product was purified by column chromatography (EtOAc:MeOH=100:5) and the entitled intermediate was isolated as a white solid (180 mg, yield 90%).

後処理

  1. temperatureunder reflux
  2. extractionextracted with ethylacetate
  3. customThe product was purified by column chromatography (EtOAc:MeOH=100:5)

出典と根拠

ORDレコード
ord-5e8db0f63f75499cbb5ce68fc1a480ba
出典データセット
uspto-grants-2014_12
特許番号
US08912330B2

反応ノート

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