Sodium Carbonate → HCID 10155510, compound

HRID 1072661Notes

Reaction equation

HRID 1072661 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.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].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>[CH3:16][CH:7]([O:6][C:5]1[CH:17]=[CH:18][C:2]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)=[CH:3][CH:4]=1)[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 9840705HCID 9840705, compound

Product 1

HCID 10155510HCID 10155510, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (82 mg, 30%, yellow foam) was prepared from [2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (252 mg, 0.749 mmol, prepared in example 1), 4-formylbenzeneboronic acid (135 mg, 0.900 mmol), dichlorobis(triphenylphosphine)palladium(II) (21 mg, 0.030 mmol), 2 M sodium carbonate (270 mg in 1.3 mL water), and 1,2-dimethoxyethane (5 mL) in a manner analogous to the procedure described in Example 8.

Sources & evidence

ORD record
ord-7b0acdd57bcf4aafbddbdb3d7615b13c
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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