4-Acetyl-3-fluorophenylboronic acid → 4'-Acetyl-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

HRID 1524043Notes

Reaction equation

HRID 1524043 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][C:5]=1[F:13])(=[O:3])[CH3:2].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])(=[O:23])=[O:22]>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:15]2[C:16]([S:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])(=[O:22])=[O:23])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:6][C:5]=1[F:13])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 121330274-Acetyl-3-fluorophenylboronic acidHCID 263700292-bromo-N,N-diethylbenzenesulfonamide

Product 1

HCID 903132524'-Acetyl-N,N-diethyl-3'-fluorobiphenyl-2-sulfonamide

Procedure

The title compound was prepared using conditions analogous to those described in Example 1 using (4-acetyl-3-fluorophenyl)boronic acid and 2-bromo-N,N-diethylbenzenesulfonamide. MS (ESI): mass calcd. for C18H20FNO3S, 349.11; m/z found, 350.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.05 (dd, J=7.9, 1.2, 1H), 7.92 (m, 1H), 7.61-7.56 (m, 1H), 7.55-7.49 (m, 1H), 7.29-7.27 (m, 2H), 7.25-7.24 (m, 1H), 2.95 (q, J=7.1, 4H), 2.69 (d, J=4.9, 3H), 1.01 (t, J=7.1, 6H).

Sources & evidence

ORD record
ord-dd9b0fab6331428880ac5ce954d96899
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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