3-Nitrophenylboronic Acid → 2-Ethyl-7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one

HRID 1007100Notes

Reaction equation

HRID 1007100 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7](=[O:12])[CH:8]([CH2:10][CH3:11])[S:9][C:4]=2[CH:3]=1.[N+:15]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.O.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>[CH2:10]([CH:8]1[C:7](=[O:12])[NH:6][C:5]2[CH:13]=[CH:14][C:2]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:23]=3)=[CH:3][C:4]=2[S:9]1)[CH3:11]

Participants

8

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 226677487-bromo-2-ethyl-4H-benzo[1,4]thiazin-3-one

Product 1

HCID 98833222-Ethyl-7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-oneYield 7.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 7-bromo-2-ethyl-4H-benzo[1,4]thiazin-3-one (2 g, 7.3 mmol), 3-nitrophenyl boronic acid (1.22 g, 7.3 mmol), potassium carbonate (3 g, 22 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.84 g, 0.72 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc (3×40 mL). The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated. The residue was recrystallized from ethanol to afford the title compound as tan crystals (0.17 g, 7.3%): mp 180° C.; MS (EI) m/z 314 (M+).

Workup

  1. temperatureto reflux for 6 hours
  2. extractionextracted with EtOAc (3×40 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-35771439dda347bd803c68a50697ec29
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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