Potassium Carbonate → HCID 11681522, compound
Reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[C:18]([C:21]1[CH:26]=[C:25]([C:2]2[CH:17]=[CH:16][C:5]([O:6][C:7]3[N:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
The general procedure described in Example 3 was used with 2-(4-chloro-phenoxy)-nicotinic acid (250 mg, 1.00 mmol), 3-acetylphenylboronic acid (246 mg, 1.50 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (414 mg, 3.00 mmol), water (2.0 mL), 12 h, 80° C. The product was isolated as a white solid (305 mg, 92%). Mp=188° C. 1H NMR (400 MHz, d 6-DMSO) δ: 8.27 (m, 2H), 8.20 (s, 1H), 7.93 (d, 2H, J=7.6 Hz), 7.77 (d, 2H, J=8.8 Hz), 7.61 (t, 1H, J=7.6 Hz), 7.23 (m, 3H), 2.66 (s, 3H). 13C NMR (125 MHz, d6-DMSO) δ: 198.0, 166.0, 160.7, 153.9, 150.3, 141.5, 140.0, 137.5, 135.6, 131.3, 129.4, 128.2, 126.9, 126.4, 121.9, 119.1, 117.2, 26.9. IR (neat, cm−1): 3000-4000 (br), 1674, 1651, 1585, 1418, 1231, 896, 770. Anal. Calcd for C20H15NO4: C, 72.06; H, 4.54. Found: C, 71.68; H, 4.41.
Sources & evidence
- ORD record
- ord-d30de543e0e8443985f2bcc36eb57122
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560596B2
Reaction notes
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