4-Acetyl-3-fluorophenylboronic acid → 1-[3-Fluoro-2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl]ethanone

HRID 1524044Notes

Reaction equation

HRID 1524044 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]1[CH2:28][CH2:27][CH2:26][CH2:25]1)(=[O:23])=[O:22]>>[F:13][C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)(=[O:23])=[O:22])[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 121330274-Acetyl-3-fluorophenylboronic acidHCID 256321041-(2-Bromobenzene-1-sulfonyl)pyrrolidine

Product 1

HCID 903134931-[3-Fluoro-2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl]ethanone

Procedure

The title compound was prepared using conditions analogous to those described in Example 1 using (4-acetyl-3-fluorophenyl)boronic acid and 1-(2-bromo-phenylsulfonyl)pyrrolidine. MS (ESI): mass calcd. for C18H18FNO3S, 347.10; m/z found, 348.0 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.10 (dd, J=7.9, 1.3, 1H), 7.95-7.89 (m, 1H), 7.63-7.58 (m, 1H), 7.58-7.51 (m, 1H), 7.30-7.27 (m, 2H), 7.26-7.25 (m, 1H), 2.98-2.90 (m, 4H), 2.69 (d, J=4.9, 3H), 1.76-1.67 (m, 4H).

Sources & evidence

ORD record
ord-01cd3fcb494d4a6fba76bf2b0c5de1ab
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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