Potassium Carbonate → 5-(4-Chlorophenyl)-6-cyclobutoxy-nicotinic acid

HRID 1958193Notes

Reaction equation

HRID 1958193 reaction equation
Br[C:2]1[C:3]([O:11][CH:12]2[CH2:15][CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.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>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[C:3]([O:11][CH:12]3[CH2:15][CH2:14][CH2:13]3)=[N:4][CH:5]=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 666788435-Bromo-6-cyclobutoxynicotinic acid

Product 1

HCID 666786185-(4-Chlorophenyl)-6-cyclobutoxy-nicotinic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-6-cyclobutoxy-nicotinic acid (example 78 a; 1.531 g, 5.63 mmol), 4-chloro-phenylboronic acid (968 mg, 6.19 mmol), potassium carbonate (1.56 g, 11.3 mmol) and tetrakis(triphenylphosphine)palladium (325 mg, 281 μmol) were suspended in THF (38 mL) and water (38 mL). The reaction mixture was stirred at reflux temperature (100° C.) over the weekend. THF was removed and the residue was partitioned between water (pH=2) and ethyl acetate; the organic phases were combined, dried with MgSO4 and concentrated in vacuo to obtain the title compound (quant.) as off-white solid; MS (ESI) 302.2 (M−H)−.

Workup

  1. customTHF was removed
  2. customthe residue was partitioned between water (pH=2) and ethyl acetate
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83b17ebdb8724c639e3d9dd946571a1a
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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