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

HRID 2264614노트

반응식

HRID 2264614 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b9001ac709f4f7289f6af0da699cdda
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855215B2

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