5-Chlorosalicylic Acid → HCID 4128459, compound

HRID 1028896Notes

Reaction equation

HRID 1028896 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)#[N:13].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:12]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=2)=[CH:16][CH:15]=1)#[N:13]

Participants

7

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 4128459HCID 4128459, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateCatalystHCID 962WaterSolvent

Procedure

The general procedure described in Example 3 was used with 5-chloro-2-hydroxy-benzoic acid (173 mg, 1.00 mmol), 4-cyanophenylboronic acid (176 mg, 1.20 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 (552 mg, 4.00 mmol), water (2.0 mL), 12 h, 80° C. The product was isolated as a white solid (220 mg, 92%). Mp=227° C. 1H NMR (400 MHz, d4-MeOH) δ: 8.11 (d, 1H, J=2.4 Hz), 7.81-7.70 (m, 5H), 7.02 (d, 1H, J=8.4 Hz). 13C NMR (125 MHz, d4-MeOH) δ: 173.2, 163.5, 145.5, 135.4, 134.0, 131.2, 130.1, 128.3, 120.1, 119.4, 114.6, 111.5. IR (neat, cm−1): 3429, 2229, 1667, 750. Anal. Calcd for C14H9NO3: C, 70.29; H, 3.79. Found: C, 69.96; H, 3.52.

Sources & evidence

ORD record
ord-10adb890726f4f6b82f3ab5a702271f0
Source dataset
uspto-grants-2014_05
Patent number
US08735630B2

Reaction notes

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