Potassium Carbonate → Isopropyl 6-(2-hydroxypropan-2-yl)-3,4'-bipyridine-2'-carboxylate

HRID 1909461Notes

Reaction equation

[CH:1]([O:4][C:5]([C:7]1[CH:12]=[C:11](B(O)O)[CH:10]=[CH:9][N:8]=1)=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:23]1[CH:24]=[CH:25][C:26]([C:29]([OH:32])([CH3:31])[CH3:30])=[N:27][CH:28]=1>C1(C)C=CC=CC=1>[OH:32][C:29]([C:26]1[N:27]=[CH:28][C:23]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH:12]=2)=[CH:24][CH:25]=1)([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of crude 2-(isopropoxycarbonyl)pyridin-4-ylboronic acid (700 mg, ˜1.0 mmol), dppf(Pd)Cl2 (40 mg, 5 mol %), potassium carbonate (280 mg, 2.0 mmol) and 2-(5-bromopyridin-2-yl)propan-2-ol (216 mg, 1.0 mmol) in degassed toluene (3 mL), degassed water (1 mL) and degassed isopropanol (1 mL) was heated at 85° C. for 1 hour. The aqueous layer was discarded and the solvent removed under reduced pressure. The residue was purified by flash chromatography (rf: 0.53 in 20:1 ethyl acetate:methanol) to give isopropyl 6-(2-hydroxypropan-2-yl)-3,4′-bipyridine-2′-carboxylate (140 mg, 47% yield). 301.1 (M+1).

Workup

customdegassed water (1 mL)
customdegassed isopropanol (1 mL)
customthe solvent removed under reduced pressure
customThe residue was purified by flash chromatography (rf: 0.53 in 20:1 ethyl acetate:methanol)

Sources & evidence

ORD record: ord-d6877ccefc894ca283aabe4c68fd59cd
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598360B2

Reaction notes

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