4-Carboxyphenylboronic Acid → 4-[5-(Trifluoroacetyl)-2-thienyl]benzoic acid

HRID 1715358Notes

Reaction equation

HRID 1715358 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.[C:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:15])=[O:14]>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:7]([C:5]1[S:6][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 199715871-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 445412324-[5-(Trifluoroacetyl)-2-thienyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The titled compound was prepared from 1-(5-bromo-2-thienyl)-2,2,2-trifluoroethanone (C2) (1.0 eq) and the corresponding 4-carboxyphenylboronic acid (1.3 eq) in DMF (1.0M) following the general procedure for Suzuki cross-coupling described in example 3 step 1. After completation of the reaction the solution mixture was concentrated under reduced pressure and 1N HCl solution was added. The resulting precipitate formed was washed several times with DCM and used in the next coupling reaction without further purification. 1H NMR (400 MHz, DMSO, 300K) δ 13.14 (1H, broad s), 8.18 (1H, broad s), 8.06-8.00 (4H, m), 7.95 (1H, d, J=4.2 Hz). MS (ES) C13H7F3O3S requires: 300, found: 301 (M+H+).

Workup

  1. customAfter completation of the reaction the solution mixture
  2. concentrationwas concentrated under reduced pressure and 1N HCl solution
  3. additionwas added
  4. customThe resulting precipitate formed
  5. washwas washed several times with DCM
  6. customused in the next coupling reaction without further purification

Sources & evidence

ORD record
ord-697df041fdc142cd855f5862a7aae11c
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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