HCID 67050668, compound → HCID 58204474, compound

HRID 2044367Notes

Reaction equation

HRID 2044367 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)=[CH:9][N:8]([C:14]1[N:18]([CH:19]([CH3:21])[CH3:20])[CH:17]=[N:16][N:15]=1)[N:7]=3>C(#N)C.[Pd]>[CH:19]([N:18]1[CH:17]=[N:16][N:15]=[C:14]1[N:8]1[N:7]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:4]3[CH:3]=[CH:2][CH:23]=[CH:22][C:5]=32)=[CH:9]1)([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 67050668HCID 67050668, compound

Product 1

HCID 58204474HCID 58204474, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

Alternatively, a degassed solution of 8-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, 0.326 mmol) in IMS (10 mL) was added 10% Pd/C (15 mg), the reaction mixture stirred under an atmosphere of hydrogen for 1 h before the reaction mixture was filtered and the filtrate concentrated in vacuo. The resultant residue was dissolved in DCM and the solution washed with water, the organic layer dried (Na2SO4), filtered and concentrated in vacuo to give a residue. The residue was dissolved in acetonitrile and water and the solution freeze dried to give 2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene as a white solid (54 mg, 56%). 1H NMR (400 MHz, CDCl3): δ 8.27-8.23 (m, 2H); 8.12 (t, J=1.02 Hz, 1H); 7.30-7.24 (m, 1H); 7.14-7.06 (m, 2H); 5.38-5.29 (m, 1H); 4.36 (t, J=5.10 Hz, 2H); 3.16 (td, J=5.10, 1.06 Hz, 2H); 1.63-1.54 (d, J=6.59 Hz, 6H). LCMS: RT=10.29 min, M+H+=296

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe resultant residue was dissolved in DCM
  4. washthe solution washed with water
  5. dry with materialthe organic layer dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. dry with materialwater and the solution freeze dried

Sources & evidence

ORD record
ord-9151fb068e954dab9b111eb18d8f85e5
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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