Allyl bromide → N-[4-(1-allyl-5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide

HRID 1591842Notes

Reaction equation

HRID 1591842 reaction equation
[C:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:20][C:21](C)([O-])[CH3:22].[K+].C(Br)C=C>>[CH2:22]([N:7]1[C:3]([C:1]#[N:2])=[CH:4][CH:5]=[C:6]1[C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:12][CH:13]=1)[CH:21]=[CH2:20]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 16051191N-[4-(5-Cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 16051275N-[4-(1-allyl-5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamideYield 6.3%

Procedure

N-[4-(5-cyano-1H-pyrrol-2-yl)phenyl]ethanesulfonamide (0.150 g, 0.54 mmol) was alkylated according to the procedure of Example 40 using potassium tert-butoxide (1.08 mL of a 1M solution, 1.08 mmol) and allyl bromide (0.041 mL, 0.50 mmol) to afford the title compound (0.10 g, 6.3%).

Sources & evidence

ORD record
ord-5340ebd9eeea4394bc0b0d975a79f05b
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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