Ethyl 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoate → 4-(5-Bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 533532Notes

Reaction equation

HRID 533532 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([O:13]CC)=[O:12])=[N:6][CH:7]=1.BrC1C=CC(CCC(C)(S(C)(=O)=O)C(O)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 57326698Ethyl 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoateHCID 66577906(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid

Product 1

HCID 665778654-(5-Bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoic acidYield 93%

Procedure

The title compound (1740 mg, 93%) was prepared from ethyl 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoate (2025 mg, 5.6 mmol) by a procedure analogous to that described for the preparation of compound (II) 4-(6-bromophenyl-3-yl)-2-methyl-2-(methylsulfonyl)butanoic acid, Preparation 2, step 3. MS (LCMS) m/z 336.1 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.63 (s, 3H) 2.25 (ddd, J=13.27, 11.71, 5.07 Hz, 1H) 2.58 (ddd, J=13.27, 11.32, 5.07 Hz, 1H) 2.70-2.81 (m, 1H) 2.88-2.99 (m, 1H) 3.10 (s, 3H) 7.27 (d, J=8.20 Hz, 1H) 7.86-7.92 (m, 1H) 8.53 (d, J=1.95 Hz, 1H).

Sources & evidence

ORD record
ord-a2a1734bf211429580852be58d3f099f
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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