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Acetyl chloride → N-(2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide

HRID 2423184
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HRID 2423184 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[O:21][CH2:22][CH2:23][NH2:24].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[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:13])=[O:14])=[CH:5][C:4]=1[O:21][CH2:22][CH2:23][NH:24][C:32](=[O:34])[CH3:33]
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참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 672418872-{[6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine2회

생성물 1

HCID 67243162N-(2-{[6-methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethyl)acetamide수율 53.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

2-{[6-Methoxy-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine (Intermediate 32, 2.0 g, 5.8 mmol) in DCM (100 mL) was treated with triethylamine (2.4 mL, 17 mmol) and 4-dimethylaminopyridine (0.35 g, 2.9 mmol). The solution was cooled to 0° C. and acetyl chloride (0.82 mL, 12 mmol) was added. The mixture was stirred at room temperature for 1 hour, washed with aqueous saturated NaHCO3 (20 mL) and 1 M HCl (2×20 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (1.2 g). MS m/z 389 [M+H]+.

후처리

  1. washwashed with aqueous saturated NaHCO3 (20 mL) and 1 M HCl (2×20 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-07ebdb0ca7ad49c596dfdfc0fff85832
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960374B2

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