Dichloromethane → [6-(2-Hydroxypropan-2-yl)pyridin-3-yl]boronic acid

HRID 1499919Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:16][B:15](B2OC(C)(C)C(C)(C)O2)[O:14]1.ClCCl.C([O-])(=O)C.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:11][C:8]([C:5]1[N:6]=[CH:7][C:2]([B:15]([OH:16])[OH:14])=[CH:3][CH:4]=1)([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(5-bromopyridin-2-yl)propan-2-ol (70 mg, 0.3 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (90.0 mg, 0.36 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (10 mg, 0.01 mmol), and potassium acetate (100 mg, 1 mmol) in 1,4-dioxane (5 mL) was heated at 120° C. overnight. The reaction was complete by LC/MS, was concentrated in vacuo to give crude [6-(1-hydroxy-1-methylethyl)pyridin-3-yl]boronic acid. LCMS calculated for C8H13BNO3 (M+H)+: m/z=182.1; found: 182.1.

Workup

concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-44d507b1d2af42859646763adb2a963a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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