Sodium Carbonate → HCID 178489290, compound

HRID 496135Notes

Reaction equation

HRID 496135 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:10][S:11](=[O:13])(=[O:12])[C:6]=2[C:5](I)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[NH:10][S:11](=[O:13])(=[O:12])[C:6]=2[C:5]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 178527163HCID 178527163, compound

Product 1

HCID 178489290HCID 178489290, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-chloro-3-cyclohexyl-8-iodo-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (290 mg, 0.68 mmol), 2-methoxyphenylboronic acid (122 mg, 0.80 mmol), Pd(PPh3)2Cl2 (10 mg, 2 mol %) in 1,2-dimethoxyethane (50 ml) and Na2CO3 (2M, 2 ml, 4 mmol) were refluxed under N2 for 2 h. The solvents were removed under reduced pressure and the residue was extracted with EtOAc (2×40 ml) and the organic layer was washed with saturated NaHCO3 (20 ml), dried (Na2SO4) and the solvent was removed under reduced pressure. The product was purified by flash chromatography on SiO2 using EtOAc:n-hexane (1:2, v/v) as eluent, yielding 200 mg (73%) of 5-chloro-3-cyclohexyl-8-(2-methoxyphenyl)-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide as colorless crystals.

Workup

  1. temperaturewere refluxed under N2 for 2 h
  2. customThe solvents were removed under reduced pressure
  3. extractionthe residue was extracted with EtOAc (2×40 ml)
  4. washthe organic layer was washed with saturated NaHCO3 (20 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe product was purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-334821776691417193d8c8ec18c58e27
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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