Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 71739072, compound

To a solution of 6-chloropyridin-3-ol (40 g, 309 mmol, Eq: 1.00) and ethyl 2-bromo-2-methylpropanoate (63.2 g, 48.1 ml, 324 mmol, Eq: 1.05) in 300 ml of CH3 CN was added Cs2 CO3 (216 g, 664 mmol, 309 mmol, Eq: 2.15) and the resulting reaction mixture was stirred under argon atmosphere for 48 h. The reaction mixture was filtered and the filtercake was washed well with EtOAc. The combined filtrate and washes were diluted with water (300 ml) and shaken and the organic phase was collected. The aqueous phase was back-extracted with EtOAc (2×150 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by passing through a plug of 200 g of silica and elution with 30% EtOAc/Hexanes afforded the desired product (51.1 g) as a light yellow oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.27 (t, J=7.18 Hz, 3 H) 1.61 (s, 6 H) 4.24 (q, J=7.18 Hz, 2 H) 7.12-7.25 (m, 2 H) 8.01 (d, J=2.64 Hz, 1 H).

1. customthe resulting reaction mixture
2. filtrationThe reaction mixture was filtered
3. washthe filtercake was washed well with EtOAc
4. additionThe combined filtrate and washes were diluted with water (300 ml)
5. stirringshaken
6. customthe organic phase was collected
7. extractionThe aqueous phase was back-extracted with EtOAc (2×150 ml)
8. dry with materialThe combined organics were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification
12. washa plug of 200 g of silica and elution with 30% EtOAc/Hexanes

ORD record

ord-0de7b8b1ac9a4295b7a602cc4bbb46cf

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889682B2