2-Bromopyridine → HCID 178527162, compound

HRID 496137Notes

Reaction equation

HRID 496137 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](B(O)O)=[CH:4][CH:3]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.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:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 178527161HCID 178527161, compound

Product 1

HCID 178527162HCID 178527162, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-chloro-3-cyclohexyl-8-(dihydroxyboryl)-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (440 mg, 1.28 mmol), 2-bromopyridine (0.14 ml, 1.50 mmol), Pd(PPh3)2Cl2 (10 mg, 2 mol %) in 1,2-dimethoxyethane (30 ml) and Na2CO3 (2M, 3 ml, 6 mmol) were refluxed under N2 for 24 h. The solvents were removed under reduced pressure and the residue was treated with saturated NH4Cl (10 ml) and extracted with EtOAc (2×40 ml). The organic layer was washed with water (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 (2:1, v/v) as eluent, yielding 280 mg (58%) of 5-chloro-3-cyclohexyl-8-(2-pyridyl)-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide as colorless crystals.

Workup

  1. temperaturewere refluxed under N2 for 24 h
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue was treated with saturated NH4Cl (10 ml)
  4. extractionextracted with EtOAc (2×40 ml)
  5. washThe organic layer was washed with water (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-e140a232d55d4e9193502402ef7df038
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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