5-Fluoroindole-2-carboxylic acid → 5-fluoro-1H-indole-2-carboxylic acid (3-hydroxy-propyl)-amide

HRID 29783

反応式

HRID 29783 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.CCN=C=NCCCN(C)C.[NH2:25][CH2:26][CH2:27][CH2:28][OH:29]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:29][CH2:28][CH2:27][CH2:26][NH:25][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)=[O:13]

参加物

6

反応物 3

HCID 18205-Fluoroindole-2-carboxylic acidHCID 90863-Amino-1-propanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

生成物 1

HCID 597892005-fluoro-1H-indole-2-carboxylic acid (3-hydroxy-propyl)-amide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-fluoro-1H-indole-2-carboxylic acid (2.27 g, 12.7 mmol) in CH2Cl2 (100 mL) is added DMAP (4.64 g, 38 mmol), EDCI (3.64 g, 19 mmol), 3-amino-propan-1-ol (1.90 g, 25 mmol). The mixture is stirred at room temperature for 24 hours. After the solvent is removed under vacuum, 5% HCl (100 mL) is added to the mixture. It is extracted with EtOAc (100 mL×3). The combined organic layers are washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL) and dried with Na2SO4. Solvent is removed to give 5-fluoro-1H-indole-2-carboxylic acid (3-hydroxy-propyl)-amide; 1H NMR (DMSO-d6) δ 1.69 (quint, 2H, J=6.4 Hz), 3.34 (q, 2H, J=6.0 Hz), 3.48 (t, 2H, J=6.4 Hz), 4.48 (bs, 1H), 6.99-7.10 (m, 2H), 7.36-7.44 (m, 2H), 8.47 (t, 1H, J=5.6 Hz), 11.63 (s, 1H); m/z [M++1] 237.1.

後処理

  1. customAfter the solvent is removed under vacuum, 5% HCl (100 mL)
  2. additionis added to the mixture
  3. extractionIt is extracted with EtOAc (100 mL×3)
  4. washThe combined organic layers are washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. customSolvent is removed

出典と根拠

ORDレコード
ord-d9c1a501838d44b187f008901b681277
出典データセット
uspto-grants-2008_09
特許番号
US07423031B2

関連ノート

読み込み中…