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1,2-Dichloroethane → 7-Fluoro-indole-5-carboxylic acid (n-[2-hydroxy-2-(3,4,5-trimethoxyphenyl) ethyl]) amide

HRID 1976784
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HRID 1976784 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Cl.[NH2:15][CH2:16][CH:17]([C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)[OH:18].C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[OH:18][CH:17]([C:19]1[CH:20]=[C:21]([O:29][CH3:30])[C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=1)[CH2:16][NH:15][C:11]([C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][CH:8]=[CH:7]2)=[O:13]
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참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 115645587-Fluoro-1H-indole-5-carboxylic acidHCID 24194781BENZYL ALCOHOL, alpha-(AMINOMETHYL)-3,4,5-TRIMETHOXY-, HYDROCHLORIDE

생성물 1

HCID 544358387-Fluoro-indole-5-carboxylic acid (n-[2-hydroxy-2-(3,4,5-trimethoxyphenyl) ethyl]) amide

시약·촉매·용매 3

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A solution of Example 63D in DMF (10 mL)was treated sequentially with 2-amino-1-(3,4,5-trimethoxyphenyl)ethanol hydrochloric acid salt (0.343 g, 1.30 mmol), EDC (0.325 g, 1.7 mmol), triethylamine, DMAP (catalytic), heated at 50° C. for 15 hours, cooled to room temperature, poured into water (100 ml), and extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 8:2 ethyl acetate/hexanes to provide 0.24 g of the desired product.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography on silica gel with 8:2 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-87196e0cf78149cca35fdcb4ef36457b
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06228868B1

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