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Water → 2,2-Diethyl-4-[6-(3-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279123
ノート
印刷プレビュー

反応式

HRID 2279123 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[N:11]([CH2:16][C:17]2[CH:22]=[C:21](Br)[N:20]=[C:19]3[N:24]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:25]=[C:26]([CH3:27])[C:18]=23)[CH2:10][C:9]1([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:38][C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][C:44]=1[OH:45].O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[N:11]([CH2:16][C:17]2[CH:22]=[C:21]([C:41]3[CH:42]=[CH:43][C:44]([OH:45])=[C:39]([F:38])[CH:40]=3)[N:20]=[C:19]3[N:24]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][O:29]4)[N:25]=[C:26]([CH3:27])[C:18]=23)[CH2:10][C:9]1([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:7])([CH3:4])([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

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 230053613-Fluoro-4-hydroxybenzeneboronic acidHCID 900140904-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 136623246
2,2-Diethyl-4-[6-(3-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester
収率 34%

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 150 mg 4-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2,2-diethyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester and 48 mg 3-fluoro-4-hydroxy-phenylboronic acid in 8 ml of DEM and 0.45 ml of water were added 40 mg of potassium carbonate. To the degassed reaction mixture 4 mg of bis(tri-tert-butyl-phosphin)palladium(0) were added. The reaction was heated to 120° C. in a microwave reactor for 2 h. The mixture was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate twice. The combined organic layers were dried and concentrated in vacuo. The resulting residue was purified by HPLC. 53 mg (34%) of the title compound were obtained.

後処理

  1. additionwere added
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with ethyl acetate twice
  4. customThe combined organic layers were dried
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by HPLC

出典と根拠

ORDレコード
ord-0693a5f240374358bac95c4aa82bff6c
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133181B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート