Sodium hydride → HCID 86725264, 화합물

HRID 576631노트

반응식

HRID 576631 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[H-].[Na+].[C:16]([NH:23][CH2:24][CH2:25]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:25][CH2:24][NH:23][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][CH:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

생성물 1

HCID 86725264HCID 86725264, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1H-Indole-6-carboxylic acid methyl ester (0.503 g, 2.87 mmol) and DMF (9.0 mL) under argon was cooled to 0° C. for 10 min. Sodium hydride (˜48%, 0.190 g, 3.80 mmol) was added and reaction warmed to room temperature for 30 min. 2-(Boc-amino)ethyl bromide (0.787 g, 3.52 mmol) was added and the reaction stirred for 17 hr. The reaction was quenched with H2O and extracted with ethyl acetate (3×). The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (0-50% EtOAc:Hexane). ESI-MS m/z 319 (MH)+.

후처리

  1. customreaction
  2. customThe reaction was quenched with H2O
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography on silica gel (0-50% EtOAc:Hexane)

출처 및 근거

ORD 기록
ord-6eb3923a914a4473ae3ad38e63aad15d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040504B2

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