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

HRID 2423175Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][NH2:22])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][NH:22][C:30](=[O:32])[CH3:31])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-{[1-(Phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine (Intermediate 24, 9.6 g, 30 mmol) in DCM (100 mL) was treated with triethylamine (12.8 mL, 91.0 mmol) and 4-dimethylaminopyridine (1.9 g, 15 mmol). The solution was cooled to 0° C. and acetyl chloride (4.3 mL, 61 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and washed with saturated aqueous NaHCO3 (50 mL) and 1 M HCl (2×50 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (10.3 g). MS m/z 359 [M+H]+.

Workup

washwashed with saturated aqueous NaHCO3 (50 mL) and 1 M HCl (2×50 mL)
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bde581c40687401abac800fd40c6f05a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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