Sodium Carbonate → HCID 18188054, compound

HRID 1357799Notes

Reaction equation

HRID 1357799 reaction equation
Br[C:2]1[C:10]([S:11](=[O:23])(=[O:22])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=2)=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:24][CH2:25][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH3:28])[CH:3]=1.[C:35]1([CH3:44])[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.CO>[CH3:44][C:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:10]([S:11](=[O:23])(=[O:22])[NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=3)=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:24][CH2:25][CH:26]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:27][CH3:28])[CH:3]=2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 79799Tolylboronic acidHCID 18188037HCID 18188037, compound

Product 1

HCID 18188054HCID 18188054, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 21867641Toluene methanolSolvent

Procedure

from reaction of 1 eq. 4-bromo-5-(3-chloro-4-fluorobenzylsulfamoyl)-2-phenylbutylaminobenzoic acid and 1.2 eq. of 4-tolylboronic acid in a solv. mixture of toluene/MeOH 2:1 in the presence of 10 mol % of Pd(OAc)2, 20 mol % of triphenylphosphine and 3 eq. of sodium carbonate under reflux for 3 hours. Aqueous work-up, subsequent preparative HPLC and freeze-drying yields a colorless solid.

Workup

  1. customfrom reaction of 1 eq
  2. temperatureunder reflux for 3 hours
  3. customAqueous work-up, subsequent preparative HPLC and freeze-drying
  4. customyields a colorless solid

Sources & evidence

ORD record
ord-fe1f0dcf34e940a385aabe1e0aa03b29
Source dataset
uspto-grants-2003_07
Patent number
US06593352B2

Reaction notes

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