Cesium carbonate → HCID 59339828、化合物

HRID 1098990

反応式

HRID 1098990 の反応式
[NH2:1][C@H:2]([CH3:14])[C@@H:3]([C:5]1[CH:13]=[CH:12][C:8]2[CH2:9][CH2:10][O:11][C:7]=2[CH:6]=1)[OH:4].[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[C:25](=[CH:26][C:27](I)=[CH:28][CH:29]=3)[CH:24]=[N:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)CCC.[Cu]I>[O:11]1[C:7]2[CH:6]=[C:5]([C@@H:3]([O:4][C:27]3[CH:26]=[C:25]4[C:30](=[CH:29][CH:28]=3)[N:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)[N:23]=[CH:24]4)[C@@H:2]([NH2:1])[CH3:14])[CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 66812942(1R,2R)-2-amino-1-(2,3-dihydrobenzofuran-6-yl)propan-1-ol

生成物 1

HCID 59339828HCID 59339828、化合物収率 22%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8008Butyronitrile溶媒

反応条件

温度
105 °C

実験手順

A stirred mixture of (1R,2R)-2-amino-1-(2,3-dihydrobenzofuran-6-yl)propan-1-ol (306b, 180 mg, 0.93 mmol), 1-(4-fluorophenyl)-5-iodo-1H-indazole (346 mg, 1.02 mmol), and cesium carbonate (0.910 g, 2.79 mmol) in butyronitrile (2 mL) was degassed for 5 min. Then copper(I) iodide (35 mg, 190 μmol) was added. The tube was sealed and heated at 105° C. for 12 h. The solvent was removed, the residue was taken in dichloromethane (20 mL), and filtered on a prepact silica column (10 g), washed with dichloromethane (50 ml) followed by ethyl acetate (50 ml). Than the product was eluted with a mixture of 0.35M ammonia solution in ethylacetate/methanol (5:95) (100 ml) to give 80 mg (22%) of subtitle compound.

後処理

  1. customwas degassed for 5 min
  2. customThe tube was sealed
  3. customThe solvent was removed
  4. filtrationfiltered on a prepact silica column (10 g)
  5. washwashed with dichloromethane (50 ml)
  6. washThan the product was eluted with a mixture of 0.35M ammonia solution in ethylacetate/methanol (5:95) (100 ml)

出典と根拠

ORDレコード
ord-d1952ce3809d412686d9697d91bcefce
出典データセット
uspto-grants-2012_03
特許番号
US08143290B2

関連ノート

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