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Water → diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate

HRID 1748292
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HRID 1748292 반응식
[F:1][C:2]([F:35])([CH2:23]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[CH:6]=[C:5]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[N-:36]=[N+:37]=[N-:38].[Na+].O>CN(C=O)C>[N:36]([CH2:23][C:2]([F:35])([F:1])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[CH:6]=[C:5]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:37]=[N-:38]
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5

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HCID 962WaterHCID 33557Sodium AzideHCID 86682393diethyl 1-(2,2-difluoro-3-{[(4-methylphenyl)sulfonyl]oxy}propyl)-1H-indole-2,6-dicarboxylate

생성물 1

HCID 86682394diethyl 1-(3-azido-2,2-difluoropropyl)-1H-indole-2,6-dicarboxylate수율 119.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
95 °C

실험 절차

To a solution of diethyl 1-(2,2-difluoro-3-{[(4-methylphenyl)sulfonyl]oxy}propyl)-1H-indole-2,6-dicarboxylate (4.7 g, 59% pure, 5.5 mmol) in DMF (40 mL) is added sodium azide (908 mg, 13.8 mmol). The mixture is heated at 95° C. for 40 h. Water (250 mL) is added and the mixture is extracted with EtOAc (3×250 mL). The organic layers are combined, washed with water (3×250 mL), dried (Na2SO4) and concentrated to afford the title crude compound (2.5 g) which is used in the next step without purification.

후처리

  1. extractionthe mixture is extracted with EtOAc (3×250 mL)
  2. washwashed with water (3×250 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d7320d0e0dd343e9ad7f71585f952534
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150577B2

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