Sodium t-butoxide → Methyl 1-(1-(1,4-dioxan-2-yl)ethyl)-2-methyl-1H-indole-3-carboxylate

HRID 2206549Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7](/[N:9]=[C:10](\[CH3:23])/[CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1Br)[C:12]([O:14][CH3:15])=[O:13])[CH3:8].CC(C)([O-])C.[Na+]>O1CCOCC1>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7]([N:9]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]1[CH3:23])[CH3:8]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of (E)-methyl 3-((1-(1,4-dioxan-2-yl)ethyl)imino)-2-(2-bromophenyl)butanoate (400 mg, 1.1 mmol) in dioxane (3 mL) was added Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-triisopropylbiphenyl][2-(2-aminoethyl)phenyl]Pd(II) (160 mg, 0.2 mmol), 2-Dicyclohexyphosphino-2′,6′-diisopropoxybiphenyl (93 mg, 0.2 mmol) and sodium tert-butoxide (192 mg, 2 mmol). The resulting reaction mixture was heated to 120° C. with stirring for 30 mins in a microwave. The reaction mixture was quenched by adding water and was extracted with ethyl acetate (25 mL×3). The combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by column chromatograph on silica gel (eluted: petrol ether/acetic ester 10:1→5:1→2:1) to afford the title compound (282 mg, 89%) as yellow solid. LCMS (M+H+) m/z: calcd. 303.15. found 303.9.

Workup

customThe resulting reaction mixture
customThe reaction mixture was quenched
additionby adding water
extractionwas extracted with ethyl acetate (25 mL×3)
dry with materialThe combined organic phase was dried by anhydrous sodium sulphate
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by column chromatograph on silica gel (eluted: petrol ether/acetic ester 10:1→5:1→2:1)

Sources & evidence

ORD record: ord-be2036b2fc3b42008bacb75e42a68a94
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

Loading…