5-Carboxypyridine-3-boronic acid → 5-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)nicotinic acid

HRID 1397381Notes

Reaction equation

HRID 1397381 reaction equation
Br[C:2]1[S:6][C:5]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.B([C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH:24]=1)[C:21]([OH:23])=[O:22])(O)O>>[F:9][C:8]([F:11])([F:10])[C:7]([C:5]1[S:6][C:2]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([CH:24]=2)[C:21]([OH:23])=[O:22])=[CH:3][CH:4]=1)=[O:12]

Participants

3

Reactant 2

HCID 35605035-Carboxypyridine-3-boronic acidHCID 199715871-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 673255045-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)nicotinic acidYield 82%

Procedure

This compound was synthesized from 1-(5-bromothiophen-2-yl)-2,2,2-trifluoroethanone and 5-borononicotinic acid as described in example 88 step 3 (470 mg, yield 82%). 1H NMR (300 MHz, DMSO-d6) δ 13.74 (br s, 1H), 9.30-9.29 (s, 1H), 9.11-9.10 (m, 1H), 8.59-8.58 (t, J=2.0 Hz, 1H), 8.20-8.19 (m, 1H), 8.07-8.05 (m, 1H).

Sources & evidence

ORD record
ord-52544b810d914fa2bb7a372683d121a1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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