Diisopropylethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenoxy)benzamide

HRID 1777700ノート

反応式

HRID 1777700 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH2:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH:31][C:10](=[O:12])[C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=2)=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225734424-(3-Fluorophenoxy)benzoic acid

生成物 1

HCID 67974035N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenoxy)benzamide収率 20.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(3-fluorophenoxy)benzoic acid (0.180 g, 0.775 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.180 g; 0.775 mmol), HATU (0.324 g; 0.852 mmol) and N,N-diisopropylethylamine (0.334 mL; 1.94 mmol) in DMF (5 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane and 20 to 100% ethyl acetate in heptane) to yield 0.065 g (20%) of the title compound as a white solid.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in dichloromethane and 20 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-c31136d654284f9da85f89c650bdc38c
出典データセット
uspto-grants-2016_02
特許番号
US09266832B2

反応ノート

読み込み中…