Sodium Carbonate → HCID 10291372, compound

HRID 1072658Notes

Reaction equation

HRID 1072658 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([CH3:16])[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[CH3:14][CH:13]([S:10]([NH:9][CH2:8][CH:7]([O:6][C:5]1[CH:17]=[CH:18][C:2]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH3:19])=[CH:3][CH:4]=1)[CH3:16])(=[O:12])=[O:11])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 9840705HCID 9840705, compound

Product 1

HCID 10291372HCID 10291372, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (120 mg, 34%, yellow foam) was prepared from [2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (343 mg, 1.02 mmol, prepared in example 1), 2-methylbenzeneboronic acid (165 mg, 1.21 mmol), dichlorobis(triphenylphosphine)palladium(II) (30 mg, 0.043 mmol), 2 M sodium carbonate (370 mg in 1.75 mL water), and 1,2-dimethoxyethane (6.8 mL) in a manner analogous to the procedure described in Example 8.

Sources & evidence

ORD record
ord-e022738747ac4b4daa0e400bcd2bf634
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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