2-Chloro-4-(tributylstannyl)pyrimidine → 3-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

HRID 1529444ノート

反応式

HRID 1529444 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:9]=2)[N:4]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[N:3]=1.[Cl:22][C:23]1[N:28]=[C:27]([Sn](CCCC)(CCCC)CCCC)[CH:26]=[CH:25][N:24]=1>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:23]1[N:28]=[C:27]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH:9]=3)[N:4]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:3]=2)[CH:26]=[CH:25][N:24]=1

参加物

6

反応物 2

HCID 468399532-Chloro-4-(tributylstannyl)pyrimidineHCID 679599763-iodo-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide

生成物 1

HCID 867097953-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide収率 103.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-iodo-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide (3 g, 7.53 mmol) and 2-chloro-4-(tributylstannyl)pyrimidine (3.6 g, 8.04 mmol) in DMF (35 mL) under argon atmosphere was added CuI (1.7 g, 9.02 mmol) and Pd(PPh3)4 (868.5 mg, 0.75 mmol) and argon gas was bubbled for 15 min. The reaction was heated at 100° C. for 1 h. The reaction was quenched with water to give off white precipitate. The suspension filtered, washed with water and dried. The crude was purified by neutral alumina column chromatography (eluting with 100% EtOAc) to give 3-(2-chloropyrimidin-4-yl)-N,N-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxamide (3.0 g, 58%) as an off white solid. MS (ESI, pos. ion) m/z: 386.2 (M+1).

後処理

  1. customwas bubbled for 15 min
  2. customThe reaction was quenched with water
  3. customto give off white precipitate
  4. filtrationThe suspension filtered
  5. washwashed with water
  6. customdried
  7. customThe crude was purified by neutral alumina column chromatography (eluting with 100% EtOAc)

出典と根拠

ORDレコード
ord-26e7c3d818504ca88461cb725db222b8
出典データセット
uspto-grants-2015_07
特許番号
US09090593B2

反応ノート

読み込み中…