Methyl 6-bromo-5-fluoropyridine-2-carboxylate → Methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate

HRID 705190Notes

Reaction equation

HRID 705190 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12].C([Si]([O:20][C:21]1[CH:26]=[C:25]([F:27])[C:24](B2OC(C)(C)C(C)(C)O2)=[C:23]([F:37])[CH:22]=1)(C)C)(C)(C)C>>[F:27][C:25]1[CH:26]=[C:21]([OH:20])[CH:22]=[C:23]([F:37])[C:24]=1[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12]

Participants

3

Reactant 2

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylateHCID 66655007Tert-butyl(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane

Product 1

HCID 136350310Methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinateYield 65%

Procedure

Method 1 was followed using methyl 6-bromo-5-fluoropicolinate (1.0 equiv.) and tert-butyl(3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)dimethylsilane (1.75 equiv.) to give methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate in 65% yield. The reaction was heated for an additional 30 minutes at 100° C. in the microwave to drive to completion the deprotection of the TBDMS group. LC/MS=283.9 (M+H), Rt=0.69 min.

Sources & evidence

ORD record
ord-c6360913a1964feda0531de42e2683c1
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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