Phenylboronic Acid → N-Hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-phenylpyridin-2-yl)butanamide

HRID 533534Notes

Reaction equation

HRID 533534 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:11]([NH:13][OH:14])=[O:12])=[N:6][CH:7]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[OH:14][NH:13][C:11](=[O:12])[C:10]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 866687644-(5-bromopyridin-2-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Product 1

HCID 51355300N-Hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-phenylpyridin-2-yl)butanamideYield 1.3%

Procedure

The title compound (2 mg, 1%) was prepared from 4-(5-bromopyridin-2-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (151 mg, 0.43 mmol) and phenylboronic acid (79 mg, 0.65 mmol) by a procedure analogous to that described in Step F of Example 3. LCMS m/z 349.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 1.68 (s, 3H), 2.25 (m, 1H), 2.66-2.82 (m, 2H), 2.95 (m, 1H), 3.08 (s, 3H), 7.38-7.51 (m, 4H), 7.63-7.66 (m, 2H), 8.02 (dd, J=8.1, 2.3 Hz, 1H), 8.71 (dd, J=2.4, 0.8 Hz, 1H).

Sources & evidence

ORD record
ord-4904302b531c40cea91cb8b91827a755
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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