Trifluoroacetic acid → HCID 15604053, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[CH:11]=[C:12]([NH:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:13]=[C:14]([O:16]CC4C=CC(OC)=CC=4)[CH:15]=3)=[CH:7][CH:8]=[CH:9][C:2]1=2.C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:10]3[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([NH:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:11]=3)=[CH:7][CH:8]=[CH:9][C:2]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
[3-benzo[b]thiophen-4-yl-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-3-yl-amine (35 mg, 0.08 mmol) was dissolved in CH2Cl2 (1 mL) and thioanisole (188 μL, 1.60 mmol) was added. The solution was cooled to 0° C. and trifluoroacetic acid (0.1 mL) was added. The reaction mixture was stirred at room temperature for 5 h and was then quenched with water (3 mL). Sat. NaHCO3 solution was added until pH 7 and the mixture was extracted with CH2Cl2 (4×10 mL). The combined organics were washed with brine (5 mL), dried (Na2SO4) and concentrated. Flash chromatography (SiO2, CH2Cl2/MeOH 95:5) provided 3-benzo[b]thiophen-4-yl-5-(pyridin-3-ylamino)-phenol (17 mg, 58%). 3-Benzo[b]thiophen-4-yl-2-(4-methoxy-benzyl)-5-(pyridin-3-ylamino)-phenol was also isolated from this reaction. 3-Benzo[b]thiophen-4-yl-5-(pyridin-3-ylamino)-phenol 1H NMR (300 MHz, methanol-d4): δ 8.2 (d, 1H), 7.8 (d, 1H), 7.7 (d, 1H), 7.45 (d, 1H), 7.4 (two d, 2H), 7.2 (m, 2H), 7.1 (dd, 1H), 6.4 (s, 1H), 6.35 (s, 1H), 6.3 (s, 1H).
Workup
- customwas then quenched with water (3 mL)
- additionSat. NaHCO3 solution was added until pH 7
- extractionthe mixture was extracted with CH2Cl2 (4×10 mL)
- washThe combined organics were washed with brine (5 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-582ddb996ddd4c0bb4300f2ed1efe680
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504401B2
Reaction notes
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