Diisobutylaluminumhydride → 5-(6-Dihydroxymethyl-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 2264614ノート

反応式

HRID 2264614 の反応式
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22](=[O:34])[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:17][CH2:16]3)[N:9]=[CH:8][N:7]=1)=[O:5])C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.CCOC(C)=O.O>[F:32][C:30]([F:31])([F:33])[C:26]1[CH:25]=[C:24]([NH:23][C:22]([N:18]2[C:19]3[C:15](=[CH:14][C:13]([O:12][C:10]4[CH:11]=[C:6]([CH:4]([OH:5])[OH:3])[N:7]=[CH:8][N:9]=4)=[CH:21][CH:20]=3)[CH2:16][CH2:17]2)=[O:34])[CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 675312166-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid ethyl ester

生成物 1

HCID 595963845-(6-Dihydroxymethyl-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To solution of 100 mg (0.21 mMol) 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid ethyl ester (Expl. 72) in 3 ml THF at −78° C. are added 1.39 ml of a 1 M solution of diisobutylaluminium hydride in THF. After 20 h at −78° C., the mixture is slowly warmed up to 0° C. and stirred at this temperature for 2 h. Then the mixture is diluted with EtOAc and water, the aqueous layer separeted off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and after addition of 0.25 g of SiO2 concentrated. The resulting powder is put on top of a chromatography column (SiO2; EtOAc/hexane 1:4) and the title compound eluated with EtOAc/hexane 1:1: MS: [M+1]+=446; HPLC: AtRet=13.0.

後処理

  1. extractionextracted twice with EtOAc
  2. washThe organic phases are washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. additionafter addition of 0.25 g of SiO2
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-4b9001ac709f4f7289f6af0da699cdda
出典データセット
uspto-grants-2010_12
特許番号
US07855215B2

反応ノート

読み込み中…