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

HRID 521923Notes

Reaction equation

HRID 521923 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]([OH:39])([CH3:38])[CH3:37])[CH:23]=[C:24]([F:35])[C:25]=1B1OC(C)(C)C(C)(C)O1.Br[C:41]1[N:46]=[C:45]([C:47]([O:49]C)=[O:48])[CH:44]=[CH:43][C:42]=1[F:51]>>[F:35][C:24]1[CH:23]=[C:22]([C:36]([OH:39])([CH3:37])[CH3:38])[CH:21]=[C:20]([F:19])[C:25]=1[C:41]1[N:46]=[C:45]([C:47]([OH:49])=[O:48])[CH:44]=[CH:43][C:42]=1[F:51]

Participants

4

Reactant 3

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylateHCID 706551562-(3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol2×HCID 834100432-(2,6-Difluoro-4-methoxyphenyl)thiazole-4-carboxylic acid

Product 1

HCID 666524436-(2,6-Difluoro-4-(2-hydroxypropan-2-yl)phenyl)-5-fluoropicolinic acid

Procedure

Following the procedure of Intermediate 104, replacing 2,6-difluoro-4-methoxyphenylboronic acid with 2-(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (Intermediate 107) 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-f31e414781d946bfb0737d69cde6f6ee
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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