Trifluoroacetic acid → 2-(5-Bromobenzo[d]oxazole-2-carboxamido)-4-(4-chlorophenyl)thiophene-3-carboxylic acid

HRID 390777Notes

Reaction equation

HRID 390777 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[S:14][CH:15]=[C:16]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[C:17]=3[C:18]([O:20]C(C)(C)C)=[O:19])=[O:11])=[N:7][C:6]=2[CH:32]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[S:14][CH:15]=[C:16]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[C:17]=3[C:18]([OH:20])=[O:19])=[O:11])=[N:7][C:6]=2[CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67207536Tert-butyl 2-(5-bromobenzo[d]oxazole-2-carboxamido)-4-(4-chlorophenyl)thiophene-3-carboxylate

Product 1

HCID 595359892-(5-Bromobenzo[d]oxazole-2-carboxamido)-4-(4-chlorophenyl)thiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3A in DCM (2 ml) at room was added TFA (2 ml). The mixture was stirred at room temperature for 30 minutes. The solvent was removed under vacuum. The residue was suspended in DCM (1 ml). The solid was collected by filtration, washed with DCM (3×1 ml) and dried to give 4A. 1H NMR (DMSO-d6) δ 7.12 (s, 1H), 7.38 (d, 2H), 7.43 (d, 2H), 7.79 (dd, 1H), 7.96 (d, 1H), 8.29 (d, 1H), 12.80 (bs, 1H), 13.44 (b, 1H).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationThe solid was collected by filtration
  3. washwashed with DCM (3×1 ml)
  4. customdried

Sources & evidence

ORD record
ord-e4b1f33ff35940938516770c267fb1e6
Source dataset
uspto-grants-2013_02
Patent number
US08383670B2

Reaction notes

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