Methyl 6-bromo-5-fluoropyridine-2-carboxylate → 6-(2,6-Difluoro-4-(1-hydroxycyclobutyl)phenyl)-5-fluoropicolinic acid

HRID 521924Notes

Reaction equation

HRID 521924 reaction equation
FC1C=C(OC)C=C(F)C=1C1SC=C(C(O)=O)N=1.[F:19][C:20]1[CH:21]=[C:22]([C:36]2([OH:40])[CH2:39][CH2:38][CH2:37]2)[CH:23]=[C:24]([F:35])[C:25]=1B1OC(C)(C)C(C)(C)O1.Br[C:42]1[N:47]=[C:46]([C:48]([O:50]C)=[O:49])[CH:45]=[CH:44][C:43]=1[F:52]>>[F:35][C:24]1[CH:23]=[C:22]([C:36]2([OH:40])[CH2:37][CH2:38][CH2:39]2)[CH:21]=[C:20]([F:19])[C:25]=1[C:42]1[N:47]=[C:46]([C:48]([OH:50])=[O:49])[CH:45]=[CH:44][C:43]=1[F:52]

Participants

4

Reactant 3

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylateHCID 706551101-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol2×HCID 834100432-(2,6-Difluoro-4-methoxyphenyl)thiazole-4-carboxylic acid

Product 1

HCID 706554226-(2,6-Difluoro-4-(1-hydroxycyclobutyl)phenyl)-5-fluoropicolinic acid

Procedure

Following the procedure of Intermediate 104, replacing 2,6-difluoro-4-methoxyphenylboronic acid with 1-(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol (Intermediate 108) and replacing methyl 2-bromothiazole-4-carboxylate with methyl 6-bromo-5-fluoropicolinate (see US2012/225062) gave the title compound.

Sources & evidence

ORD record
ord-efd66030fc7840e58df1e43db015aa0f
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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