Potassium Carbonate → HCID 66995115, compound

HRID 1160832Notes

Reaction equation

HRID 1160832 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:17]2[S:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1OS(C(F)(F)F)(=O)=O)#[N:2].C(=O)([O-])[O-].[K+].[K+].O.[NH2:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1>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.C1(C)C=CC=CC=1>[NH2:33][C:34]1[CH:39]=[C:38]([C:8]2[CH:7]=[CH:6][C:5]([C:17]3[S:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:18]=3)=[CH:4][C:3]=2[C:1]#[N:2])[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 86618071HCID 86618071, compound

Product 1

HCID 66995115HCID 66995115, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A toluene (0.5 ml) suspension of 20 mg of methyl 5-(3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)thiophene-2-carboxylate and 10 mg of potassium carbonate was added to 15 mg of 3-aminobenzeneboronic acid monohydrate, and in an argon atmosphere, 8 mg of tetrakis(triphenylphosphine)palladium was added thereto. The mixture was stirred overnight at 100° C., then cooled to room temperature, and filtered through Celite. The solvent was evaporated under reduced pressure to obtain methyl 5-(3′-amino-2-cyanobiphenyl-4-yl)thiophene-2-carboxylate.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through Celite
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f4e0af7745e4c5b9d837d872ad66507
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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