Potassium Carbonate → (3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol

HRID 539895ノート

反応式

HRID 539895 の反応式
C[CH:2]([C:4]1[C:5]([CH3:16])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11](Cl)[N:10]=2)[CH:8]=1)[OH:3].[CH3:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:16][C:5]1[C:4]([CH2:2][OH:3])=[CH:8][N:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:27][C:23]3[CH:22]=[C:21]4[C:26](=[CH:25][CH:24]=3)[N:18]([CH3:17])[CH:19]=[CH:20]4)[N:10]=2)[N:6]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27695641-methyl-1H-indol-5-amineHCID 86698986methyl (1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanol

生成物 1

HCID 86698985(3-methyl-1-(2-(1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-1H-pyrazol-4-yl)methanol収率 40.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A round bottomed flask was charged with methyl (1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methanol (400 mg, 1.78 mmol), 1-methyl-1H-indol-5-amine (338 mg, 1.3 equiv.), potassium carbonate (0.74 g, 3.0 equiv), palladium acetate (40 mg, 0.1 equiv), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (Xantphos, 206 mg, 0.2 equiv.) and 40 mL of anhydrous dioxane. After being degassed by nitrogen bubbling, the reaction mixture was heated at 100° C. for 12 hours. Volatiles were removed in vacuo and then the resulting residue was extracted with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by recrystallization in acetonitrile to give 241 mg (36%) of the desired product as a brown solid. MS (ESI) m/z 335 [M+H]+.

後処理

  1. customAfter being degassed by nitrogen bubbling
  2. customVolatiles were removed in vacuo
  3. extractionthe resulting residue was extracted with ethyl acetate
  4. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by recrystallization in acetonitrile

出典と根拠

ORDレコード
ord-118ac1641f814d1089209b3e5e601e46
出典データセット
uspto-grants-2014_10
特許番号
US08871778B2

反応ノート

読み込み中…