3-Bromopyridine → Ethyl 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoate

HRID 533531Notes

Reaction equation

HRID 533531 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9]I)=[N:6][CH:7]=1.[CH2:11]([O:13][C:14](=[O:22])[CH:15]([S:17]([CH2:20]C)(=[O:19])=[O:18])[CH3:16])[CH3:12].BrC1C=NC=CC=1.BrC1C=CC(CCC(C)(S(C)(=O)=O)C(OCC)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:15]([CH3:16])([S:17]([CH3:20])(=[O:18])=[O:19])[C:14]([O:13][CH2:11][CH3:12])=[O:22])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 122863-BromopyridineHCID 56950323Ethyl 4-(4-bromophenyl)-2-methanesulfonyl-2-methylbutanoateHCID 61721120Ethyl 2-(ethylsulfonyl)propanoateHCID 665779095-Bromo-2-(2-iodoethyl)pyridine

Product 1

HCID 57326698Ethyl 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoateYield 49%

Procedure

The title compound (2030 mg, 49%) was prepared from 5-bromo-2-(2-iodoethyl)pyridine (3571 mg, 11.5 mmol) and (+/−)-2-ethanesulfonyl-propionic acid ethyl ester (2270 mg, 12.6 mmol) by a procedure analogous to that described for the preparation of compound (1) from Preparation 2, Step 2, i.e. (+/−)-ethyl 4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoate. MS (LC MS) m/z 364.0 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.31 (t, J=7.03 Hz, 3H) 1.68 (s, 3H) 2.28-2.39 (m, 1H) 2.54-2.76 (m, 2H) 2.83-2.95 (m, 1H) 3.05 (s, 3H) 4.24 (q, J=7.29 Hz, 2H) 7.05 (d, J=8.59 Hz, 1H) 7.71 (dd, J=8.20, 2.34 Hz, 1H) 8.56 (d, J=1.95 Hz, 1H).

Sources & evidence

ORD record
ord-ac803d5a52574b1e89b46748495b061b
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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