Cesium carbonate → HCID 59560030, compound

HRID 1643538Notes

Reaction equation

HRID 1643538 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:8]=[C:9]2[O:13][CH:12]([CH3:14])[CH2:11][C:10]=12)=[O:4].[CH3:26]S(C1C=CC(F)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:8]2[CH2:14][C:12]([CH3:26])([CH3:11])[O:13][C:9]=2[CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 59560030HCID 59560030, compound

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-fluorophenyl methyl sulfone (115 mg, 0.77 mmol), Cs2CO3 (507 mg, 1.54 mmol), and methyl 6-hydroxyl-2-methyl-2,3-dihdrovenzofuran-4-carboxylate (3e) (171 mg, 0.77 mmol). Purification by column chromatography eluting with 15-40% EtOAc in hexanes gave a pale brown solid (230 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ 7.88-7.94 (m, 2 H) 7.09 (d, J=2.53 Hz, 1 H) 7.05 (d, J=8.84 Hz, 2 H) 6.66 (d, J=2.53 Hz, 1 H) 3.81 (s, 3 H) 3.07 (s, 3 H) 2.92 (s, 2 H) 1.33 (s, 6 H); LCMS for C19H20O6S m/z 377.10 (M+H)+.

Workup

  1. customPurification by column chromatography
  2. washeluting with 15-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-939631422e2148bbad12273ac5474038
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…