Hydrochloric Acid → (5-(Benzyloxy)-6-(trifluoromethyl)pyridin-3-yl)boronic acid

HRID 634432Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:16]([F:19])([F:18])[F:17])=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)[O:24][B:23](B2OC(C)(C)C(C)(C)O2)[O:22]1.C([O-])(=O)C.[K+].Cl>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]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([B:23]([OH:24])[OH:22])[CH:12]=[N:11][C:10]=1[C:16]([F:19])([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-(benzyloxy)-5-bromo-2-(trifluoromethyl)pyridine (Intermediate G25.2, 521 mg, 1.569 mmol) in dry 1,4 dioxane (10 ml), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (438 mg, 1.726 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (344 mg, 0.471 mmol) and potassium acetate (462 mg, 4.71 mmol) were added and the suspension was stirred at 90° C. overnight. Then, HCl 4 N was added (10 mL) and the solution was stirred overnight. The solvent was removed under reduced pressure and crude was purified by C18 flash chromatography Snap 30 g eluent ((H2O/ACN)) 95:5+0.1% HCOOH}:{(ACN/H2O) 95:5+HCOOH 0.1%} from 95:5 to 0:100 affording the title compound (400 mg, 1.347 mmol, 86% yield) a white solid.

Workup

stirringthe solution was stirred overnight
customThe solvent was removed under reduced pressure and crude
customwas purified by C18 flash chromatography Snap 30 g eluent ((H2O/ACN)) 95:5+0.1% HCOOH

Sources & evidence

ORD record: ord-550aa118a4a348c9b8e337a057a25f94
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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