Potassium Carbonate → Ethyl6-(3-hydroxyphenyl)pyridine-3-carboxylate

HRID 2307561Notes

Reaction equation

HRID 2307561 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.I[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10891136Ethyl6-iodonicotinoateHCID 22606941(3-(Methoxymethoxy)phenyl)boronic acid

Product 1

HCID 22606943Ethyl6-(3-hydroxyphenyl)pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 1(h), by reaction of 1 g (6.7 mmol) of 3-methoxymethoxyphenylboronic acid (described in Example l(g)) and 1.5 g (5.6 mmol) of ethyl 6-iodonicotinate with 5.6 mL of 2.0M potassium carbonate and 320 mg of tetrakis(triphenylphosphine)palladium, followed by deprotection in ethanol, the desired product is obtained in the form of a white solid (m=354 mg; Y=26%).

Sources & evidence

ORD record
ord-9aa6332d9ba946829586647fdc9327ce
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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