Triethylamine → Methyl 5-(3-cyano-4-hydroxyphenyl)-3-fluorothiophene-2-carboxylate

HRID 562897Notes

Reaction equation

HRID 562897 reaction equation
Br[C:2]1[C:3]([F:27])=[C:4]([C:23]([O:25][CH3:26])=[O:24])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[C:9]([C:21]#[N:22])[CH:8]=1.C(N(CC)CC)C>O1CCOCC1.[C].[Pd]>[C:21]([C:9]1[CH:8]=[C:7]([C:6]2[S:5][C:4]([C:23]([O:25][CH3:26])=[O:24])=[C:3]([F:27])[CH:2]=2)[CH:12]=[CH:11][C:10]=1[OH:13])#[N:22]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66995012Methyl 4-bromo-5-(4-benzyloxy-3-cyanophenyl)-3-fluorothiophene-2-carboxylate

Product 1

HCID 66995137Methyl 5-(3-cyano-4-hydroxyphenyl)-3-fluorothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Benzyloxy-3-cyanophenyl)boronic acid and methyl 4,5-dibromo-3-fluorothiophene-2-carboxylate were dissolved in a mixed solution of toluene and a 1M aqueous sodium carbonate solution and the whole was heated at 110° C. for 2.5 days in the presence of tetrakis(triphenylphosphine)palladium to obtain methyl 4-bromo-5-(4-benzyloxy-3-cyanophenyl)-3-fluorothiophene-2-carboxylate. Methyl 4-bromo-5-(4-benzyloxy-3-cyanophenyl)-3-fluorothiophene-2-carboxylate and triethylamine were stirred at room temperature in 1,4-dioxane under a hydrogen atmosphere at normal pressure in the presence of palladium-carbon to obtain methyl 5-(3-cyano-4-hydroxyphenyl)-3-fluorothiophene-2-carboxylate. FN: 276.

Sources & evidence

ORD record
ord-794480bc564c4fe0a29e9320e22eaff9
Source dataset
uspto-grants-2011_11
Patent number
US08067446B2

Reaction notes

Loading…