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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
ノート
印刷プレビュー

反応式

HRID 1976784 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-87196e0cf78149cca35fdcb4ef36457b
出典データセット
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06228868B1

反応ノート

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