Potassium Phosphate, Tribasic → 2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-methoxy-6-nitro-pyridine

HRID 1054418Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[N:3]=1.[O:13]1[C:18]2[CH:19]=[CH:20][C:21](B(O)O)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1.CC(N(C)C)=O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O>[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([C:2]3[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[N:3]=3)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 150 °C

Procedure

2-Bromo-3-methoxy-6-nitro-pyridine (0.5 g, 2.14 mmol), 1,4-benzodioxane-6-boronic acid (0.5 g, 2.79 mmol) and a mixture of dimethylacetamide/water (10 mL/3 mL) were added to a microwave tube containing potassium phosphate (0.91 g, 4.29 mmol) and palladium tetrakistriphenylphosphine (0.4 g, 0.2 mmol) and the reaction was heated to 150° C. for 10 min. The solution was added in a separating funnel and water and ethyl acetate were added. The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organics were washed with water (*2) then brine, dried over magnesium sulphate and concentrated in vacuo. The crude was used without further purification (0.48 g, 77%). LCMS Method: 2: RT: 4.41 min, MI: 289 [M+1].

Workup

additionwere added to a microwave tube
additionThe solution was added in a separating funnel
customThe organic layer was separated
extractionthe aqueous was extracted again with ethyl acetate
washThe combined organics were washed with water (*2)
dry with materialbrine, dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe crude was used without further purification (0.48 g, 77%)

Sources & evidence

ORD record: ord-5ac1729f0c864c2ea9c736d6e42a8af6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394301B2

Reaction notes

Loading…