Acetyl chloride → HCID 67242310, compound

HRID 2423180Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][C:3]=1[O:20][CH2:21][CH2:22][NH2:23].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:13])=[CH:4][C:3]=1[O:20][CH2:21][CH2:22][NH:23][C:31](=[O:33])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

2-{[6-Fluoro-1-(phenylsulfonyl)-1H-indol-5-yl]oxy}ethanamine (Intermediate 29, 2.0 g 6.0 mmol) in DCM (100 mL) was treated with triethylamine (2.5 mL, 18 mmol) and 4-dimethylaminopyridine (0.37 g, 3.0 mmol). The solution was cooled to 0° C. and treated with acetyl chloride (0.85 mL, 12 mmol). The mixture was stirred at room temperature for 1.5 hours and washed with saturated aqueous NaHCO3 (40 mL) and 0.5 M HCl (40 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (2.0 g). MS m/z 377 [M+H]+.

Workup

washwashed with saturated aqueous NaHCO3 (40 mL) and 0.5 M HCl (40 mL)
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2df6d752b2484b0fae4e855fd8391ec4
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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