Sodium Carbonate → HCID 22388585, compound

HRID 1072654Notes

Reaction equation

HRID 1072654 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.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 9840705HCID 9840705, compound

Product 1

HCID 22388585HCID 22388585, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound (125 mg, 38%) was prepared from [2-(4-bromophenoxy)propyl][(methylethyl)sulfonyl]amine (300 mg, 0.89 mmol, prepared in example 1), 2-chlorobenzeneboronic acid (170 mg, 1.09 mmol), tetrakis(triphenylphosphine)palladium(0) (5.6 mg, 0.005 mmol), 2 M sodium carbonate (320 mg in 1.5 mL water) and 1,4-dioxane (9 mL) in a manner analogous to the procedure described in Example 2.

Sources & evidence

ORD record
ord-4a0719dbf62c4d24837528e0f45d9d6f
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

Loading…