5-Boronothiophene-2-carboxylic acid → 5-(6-((3-(2-Oxopyrrolidin-1-yl)propyl)amino)imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylic acid

HRID 870665Notes

Reaction equation

HRID 870665 reaction equation
B([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(O)O.Br[C:13]1[N:17]2[N:18]=[C:19]([NH:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][C:27]3=[O:31])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1>>[O:31]=[C:27]1[CH2:28][CH2:29][CH2:30][N:26]1[CH2:25][CH2:24][CH2:23][NH:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([C:4]3[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=3)=[CH:14][N:15]=2)[N:18]=1

Participants

3

Reactant 2

HCID 27798075-Boronothiophene-2-carboxylic acidHCID 686481591-(3-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one

Product 1

HCID 866963645-(6-((3-(2-Oxopyrrolidin-1-yl)propyl)amino)imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylic acidYield 64%

Procedure

The Suzuki coupling of 5-boronothiophene-2-carboxylic acid and 1-(3-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)propyl)pyrrolidin-2-one using the procedure described in example 5.6.19 yielded 64% of the titled compound.

Sources & evidence

ORD record
ord-e1a63cf5c83c49deb344d5159ee5ce41
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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