Sodium Bicarbonate → HCID 178519691, compound

HRID 419149Notes

Reaction equation

HRID 419149 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:21]3[C:22]([O:27]C)=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C([O-])(O)=O.[Na+]>Br.CC(O)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([C:21]3[C:22]([OH:27])=[N:23][CH:24]=[CH:25][CH:26]=3)=[O:20])=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:30])[F:31]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 579423244-chloro-N-[5-chloro-2-(2-methoxy-pyridine-3-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzene sulfonamide

Product 1

HCID 178519691HCID 178519691, compoundYield 61.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-chloro-N-[5-chloro-2-(2-methoxy-pyridine-3-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzene sulfonamide (10 mg, mmol) in 30% HBr in AcOH (1 mL) was stirred at 50° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with water (1 mL) and treated with saturated aqueous NaHCO3 solution slowly till pH 5-6. The mixture was extracted with EtOAc (2×25 mL), dried (anhydrous Na2SO4) and concentrated. The obtained residue was column purified (SiO2, 10% MeOH in CH2Cl2) to afford 4-chloro-N-[5-chloro-2-(2-hydroxy-pyridine-3-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide (6 mg) in 61.8% yield. 1H NMR (400 MHz, CDCl3) δ 8.24 (d, 1H), 8.17 (d, 1H), 8.15 (d, 1H), 7.97 (dd, 1H), 7.72 (dd, 1H), 7.63 (d, 1H), 7.43 (dd, 1H), 6.37 (t, 1H); ESMS m/z (relative intensity): 491.9 (M+H)+ (100).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc (2×25 mL)
  3. dry with materialdried (anhydrous Na2SO4)
  4. concentrationconcentrated
  5. custompurified (SiO2, 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-11a98b5f4a6842b3b4b543959d9048dd
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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