Sodium Carbonate → HCID 11326538, compound

HRID 2298310Notes

Reaction equation

Br[C:2]1[C:6](=[O:7])[C:5]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1.C(O)C>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:3]2[O:4][C:5]3([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[C:6](=[O:7])[C:2]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 90 °C

Procedure

To 102 mg of 3-bromo-2-{4-(methylsulfonyl)phenyl}-1-oxa-spiro[4,5]dec-2-en-4-one dissolved in 3 ml toluene and 15 ml ethanol, were added 16 mg of tetrakis(triphenylphosphin)palladium(0), 3 ml of 2 M aqueous sodium carbonate and 35 mg of benzeneboronic acid. The reaction mixture was stirred at 90° C. for 12 hours. The reaction mixture was then purified by a procedure similar to the procedure in Step 6 of Example 53 to afford 50 mg of 2-{4-(methylsulfonyl)phenyl}-3-phenyl-1-oxa-spiro[4,5]dec-2-en-4-one as a solid. mp: 126-127° C. NMR: δ1.77-1.85 (m, 10H), 3.06 (s, 3H), 7.27 (m, 2H), 7.35 (m, 3H), 7.83 (d, J=8.1 Hz, 2H), 7.94 (d. J=8.1 Hz, 2H). IR (cm−1): 2936, 1693, 1621, 1404, 1318, 1147, 1129, 730.

Workup

customThe reaction mixture was then purified by a procedure similar to the procedure in Step 6 of Example 53

Sources & evidence

ORD record: ord-28fa2d229daf4a649693b6d014cd5ee8
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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