3-Carboxyphenylboronic acid → HCID 67324493, compound

HRID 1397469Notes

Reaction equation

HRID 1397469 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])[S:5][CH:6]=1.[C:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([OH:15])=[O:14]>>[F:9][C:8]([F:11])([F:10])[C:7]([C:4]1[S:5][CH:6]=[C:2]([C:20]2[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])[CH:3]=1)=[O:12]

Participants

3

Reactant 2

HCID 27339573-Carboxyphenylboronic acidHCID 534079901-(4-Bromo-thiophen-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 67324493HCID 67324493, compoundYield 46%

Procedure

This compound was synthesized from 1-(4-bromothiophen-2-yl)-2,2,2-trifluoroethanone and 3-carboxyphenylboronic acid as described in example 88 step 3 (400 mg, yield 46%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.19 (br s, 1H), 8.85 (d, J=1.2 Hz, 1H), 8.50 (s, 1H), 8.29 (m, 1H), 8.10-8.08 (d, J=7.6 Hz, 1H), 7.96-7.94 (d, J=7.6 Hz, 1H), 7.62-7.59 (t, J=7.8 Hz, 1H). MS (ESI) m/z: Calculated for C13H7F3O3S: 300.01. found: 298.9 (M−H)−.

Sources & evidence

ORD record
ord-a9218075ab06471abc62b11c5625bdc5
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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