Ammonium Chloride → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

HRID 2279168ノート

反応式

HRID 2279168 の反応式
CON(C)[C:4]([C:6]1[C:7]2[C:29]([CH3:30])=[N:28][N:27]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])[CH:11]=1)=[O:5].C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]=[C:8]3[N:27]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[N:28]=[C:29]([CH3:30])[C:7]3=[C:6]([CH:4]=[O:5])[CH:11]=2)=[C:13]([F:26])[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 900139076-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde収率 113.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (1.0 g) was dissolved in THF (25 mL). At 0° C. methylmagnesium bromide solution (1 M, 3.9 mL) was added slowly, the mixture was warmed to r.t. while stirring overnight. Saturated ammonium chloride solution was added, the mixture was extracted with dichloromethane, the organic phases were dried over magnesium sulfate and concentrated in a membrane pump vacuum. The residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient) giving 1-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (1.0 g, quantitative yield with impurities).

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in a membrane pump vacuum
  4. customThe residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-2b699af02f5e405192059cc52b65d73b
出典データセット
uspto-grants-2015_09
特許番号
US09133181B2

反応ノート

読み込み中…