Hydrochloric Acid → HCID 129917368, compound

HRID 634430Notes

Reaction equation

Br[C:2]1[C:3]([CH3:10])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.CC1(C)C(C)(C)[O:15][B:14](B2OC(C)(C)C(C)(C)O2)[O:13]1.C(Cl)Cl.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]>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([B:14]([OH:15])[OH:13])[C:3]([CH3:10])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution 3-bromo-5-methoxy-2-methylpyridine (500 mg, 2.475 mmol) in dry 1,4-Dioxane (5 ml), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (691 mg, 2.72 mmol), Pd(dppf)Cl2.CH2Cl2 (606 mg, 0.742 mmol) and potassium acetate (729 mg, 7.42 mmol) were added and the solution was heated to 80° C. The reaction was stirred overnight. Then, solvent was removed and residue dissolved in THF (5.00 ml) and 12 N aqueous hydrogen chloride (4.12 ml, 49.5 mmol) was added and stirred for 3 hrs. Then, solvent was removed and the product was purified by C-18 flash chromatography (eluent ((H2O/ACN)) 95:5+0.1% HCOOH}:{(ACN/H2O) 95:5+HCOOH 0.1%} from 95:5 to 0:100 affording the title (350 mg, 2.096 mmol, 85% yield) as a white solid.

Workup

customThen, solvent was removed
dissolutionresidue dissolved in THF (5.00 ml)
stirringstirred for 3 hrs
customThen, solvent was removed
customthe product was purified by C-18 flash chromatography (eluent ((H2O/ACN)) 95:5+0.1% HCOOH

Sources & evidence

ORD record: ord-061bce0c61db4a299a5ca5cafa3b79ae
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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