N,N,N',N'-Tetramethylazodicarboxamide → 2-{[6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine

HRID 2423183노트

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HRID 2423183 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][C:4]=1[OH:21].N(C(N(C)C)=O)=NC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:54][CH2:55][NH:56]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][C:4]=1[O:21][CH2:54][CH2:55][NH2:56]

참가 물질

7

반응물 5

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 6422Trifluoroacetic acidHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 672416826-Methoxy-1-(phenylsulfonyl)-1H-indol-5-ol2회

생성물 1

HCID 672418872-{[6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine수율 110.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
150 °C

실험 절차

To 6-methoxy-1-(phenylsulfonyl)-1H-indol-5-ol (Intermediate 15, 2.0 g, 6.6 mmol), 1,1′-azobis(N,N-dimethylformamide) (2.3 g, 13 mmol), triphenylphosphine (3.5 g, 13 mmol), tert-butyl N-(2-hydroxy-ethyl)carbamate (2.1 g, 13 mmol) and DCM (40 mL) were added. The mixture was heated at 150° C. for 20 minutes in a microwave heater. The reaction mixture was allowed to cool to room temperature and TFA (30 mL) was added. The reaction mixture was allowed to stir at room temperature for 30 minutes. The solvent was removed under reduced pressure and the crude material was purified by flash chromatography on silica gel using 5% MeOH in DCM as the eluent to afford the title compound (2.53 g) MS m/z 347 [M+H]+.

후처리

  1. temperatureto cool to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe crude material was purified by flash chromatography on silica gel using 5% MeOH in DCM as the eluent

출처 및 근거

ORD 기록
ord-158f3b77cef44415a896850bbc800ec2
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960374B2

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