Water → [6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

HRID 2279117ノート

反応式

HRID 2279117 の反応式
C([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=[C:10]([Br:12])[CH:11]=1)=O)C.[BH4-].[Li+].O.C(OCC)(=O)C>C1COCC1>[Br:12][C:10]1[N:9]=[C:8]2[N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:14]=[C:15]([CH3:16])[C:7]2=[C:6]([CH2:4][OH:3])[CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 866803196-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

生成物 1

HCID 90014303[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol収率 105.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 139 mg 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]-pyridine-4-carboxylic acid ethyl ester in 8 ml of dry THF was cooled to −20° C. and 18 mg of lithium borohydride was added. After 10 min at −20° C., the reaction was slowly brought to rt. After 1.5 h at rt water and ethyl acetate were added to the reaction. The phases were separated and the organic phase was dried over sodium sulphate, filtrated and concentrated in vacuo to obtain 130 mg (98%) of the title compound as a crude product, which was used without purification in the subsequent step.

後処理

  1. customwas slowly brought to rt
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-15a7df36057c4b7da991245f2e32e5fd
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

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