Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate → Methyl 5-(N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)sulfamoyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 424000Notes

Reaction equation

HRID 424000 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:5]([NH2:18])=[CH:4][CH:3]=1.Cl[S:20]([C:23]1[N:27]([CH3:28])[C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>>[F:8][C:7]1[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])=[C:5]([NH:18][S:20]([C:23]2[N:27]([CH3:28])[C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=2)(=[O:21])=[O:22])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 2736899Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylateHCID 593863065,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

Product 1

HCID 53492226Methyl 5-(N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)sulfamoyl)-1-methyl-1H-pyrrole-2-carboxylate

Procedure

According to the general procedure B, 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)benzene1,2-diamine was reacted with methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate to obtain the title compound. 1H NMR (300 MHz, CDCl3): δ 7.37 (dd, J=1.8 & 10.5 Hz, 1H), 7.29 (m, 2H), 7.12-6.94 (m, 4H), 5.87 (dt, J=1.8, 8.4 & 17.4 Hz, 1H), 5.56 (br s, 1H), 3.65 (s, 3H), 3.75 (s, 3H).

Sources & evidence

ORD record
ord-2893275d9f1743e19b658bc9244c871f
Source dataset
uspto-grants-2012_01
Patent number
US08101799B2

Reaction notes

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