Sodium Carbonate → 6-[4-(Trifluoromethyl)phenyl]pyridine-3-carboxylic acid

HRID 1869740Notes

Reaction equation

Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

6-Chloronicotinic acid (1.57 g, 0.01 mmol), [4-(trifluoromethyl)phenyl]boronic acid (1.9 g, 0.01 mol), tetrakis(triphenylphosphine) palladium (0) (230 mg, 2 mol %), Na2CO3 (2M, 5 ml) in THF (15 ml) were placed in a microwave tube and the contents were heated in the microwave oven for 20 min at 150° C. The cooled mixture was filtered through Hyflo® to remove inorganic material, the Hyflo® was washed with EtOAc and the combined organic extracts were dispersed between aq. NaOH and EtOAc. The aqueous extracts were acidified (aq. HCl) and extracted with EtOAc; the organic extracts were washed with brine, dried (MgSO4) and evaporated to give the product (0.8 g, 30%). 1H NMR (400 MHz, CD3OD) δ: 7.85 (2H, d, J 8.2), 8.10 (1H, dd, J 0.8, 8.4), 8.31 (2H, d, J 8.2), 8.49 (1H, dd, J 2.2, 8.2), 9.26 (1H, dd, J 0.8, 2.1).

Workup

filtrationThe cooled mixture was filtered through Hyflo®
customto remove inorganic material
washthe Hyflo® was washed with EtOAc
additionthe combined organic extracts were dispersed between aq. NaOH and EtOAc
extractionextracted with EtOAc
washthe organic extracts were washed with brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-239041397f30482f8e42a1a6131fd3dd
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638629B2

Reaction notes

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