Dimethyl Sulfoxide → 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

Temperature

100 °C

A mixture of (5-bromo-2-iodo-pyridin-3-yl)-(2-methyl-allyl)-amine (10.2 g, 28.9 mmol), tetrabutylammonium chloride (9.64 g, 34.7 mmol), sodium formate (2.36 g, 34.7 mmol), palladium acetate (0.97 g, 4.3 mmol), triethylamine (8.76 g, 86.7 mmol), water (12.1 mL) and dimethyl sulfoxide (255 mL) was stirred at 100° C. under nitrogen for 1 h. The mixture was cooled by the addition of ice (100 g) then was diluted with water (200 mL) with stirring. The mixture was partitioned between water (1 L) and a mixture of toluene (600 mL) and EtOAc (50 mL). The organic phase was washed with water (4×250 mL), dried (Na2SO4) and evaporated in vacuo to give a brown oil. Chromatography (SiO2, gradient elution with 0-100% diethyl ether in 40-60 petroleum ether) gave the title compound (2.84 g) as a yellow solid. MS: [M+H]+=227, 229.

1. stirringwith stirring
2. customThe mixture was partitioned between water (1 L)
3. additiona mixture of toluene (600 mL) and EtOAc (50 mL)
4. washThe organic phase was washed with water (4×250 mL)
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo
7. customto give a brown oil
8. washChromatography (SiO2, gradient elution with 0-100% diethyl ether in 40-60 petroleum ether)

ORD record

ord-6e5cf56c8c1743b6b2c0a3ea90cd5a3b

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018214B2