Cesium carbonate → 9-bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene

HRID 2044366Notes

Reaction equation

HRID 2044366 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[C:7](=[N:8][NH:9][CH:10]=3)[C:6]=2[CH:15]=1.[CH:16]([N:19]1[CH:23]=[N:22][N:21]=[C:20]1S(C)(=O)=O)([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[C:7](=[N:8][N:9]([C:20]4[N:19]([CH:16]([CH3:18])[CH3:17])[CH:23]=[N:22][N:21]=4)[CH:10]=3)[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 582045324-isopropyl-3-methanesulfonyl-4H-[1,2,4]triazoleHCID 178419296HCID 178419296, compound

Product 1

HCID 582045089-bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azuleneYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave vial were charged 9-bromo-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene (200 mg, 0.755 mmol), 4-isopropyl-3-methanesulfonyl-4H-[1,2,4]triazole (143 mg, 0.755 mmol), cesium carbonate (246 mg, 0.755 mmol) and THF (2 mL). The reaction mixture was heated to 150° C. for 2 h then extracted with ethyl acetate (20 mL), washed with water (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 100% ethyl acetate in cyclohexane) to afford 9-bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene (122 mg, 43%). LCMS RT=4.34 min, M+H+=374/376.

Workup

  1. extractionthen extracted with ethyl acetate (20 mL)
  2. washwashed with water (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-733bb0ab00674c86bdfdf538b1966e71
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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