Ethyl Acetate → 4-(7-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2,6-dimethylpyrazolo[5,1-b]oxazol-3-yl)-3-methylphenol

HRID 1696861Notes

Reaction equation

HRID 1696861 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[C:9]([CH3:26])=[N:10][N:11]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][C:17]=4[CH3:24])=[C:14]([CH3:25])[O:13][C:12]=23)[N:3]=1.B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[C:9]([CH3:26])=[N:10][N:11]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=4[CH3:24])=[C:14]([CH3:25])[O:13][C:12]=23)[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 44816934Nvs-crf382×

Product 1

HCID 672125924-(7-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2,6-dimethylpyrazolo[5,1-b]oxazol-3-yl)-3-methylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(3,5-Dimethyl-[1,2,4]triazol-1-yl)-3-(4-methoxy-2-methyl-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole (Intermediate C) (100 mg, 0.285 mmol) was dissolved in dry DCM (5 ml). The mixture was placed under an atmosphere of flushed with N2 and treated with boron tribromide (1.423 ml, 1.423 mmol) dropwise at RT. After approximately 30 mins, the reaction was quenched by careful addition of H2O. The mixture was transferred to a separating funnel and extracted with DCM (50 ml). The organic portion was separated and washed with 1M HCl, 1M NaOH, brine, dried (MgSO4) and evaporated in vacuo to give a brown solid. Trituration with EtOAc afforded the title compound as an off white solid. LC-MS Rt 1.02 mins; MS m/z 338.2 [M+H]+; Method=2minLC—30_v002. 1H NMR (400 MHz, DMSO-d6) δ 7.25 (d, 1H), 6.8 (s, 1H), 6.75 (d, 1H), 2.35 (s, 3H), 2.30 (s, 6H), 2.2 (s, 3H), 2.15 (s, 3H).

Workup

  1. customof flushed with N2
  2. customthe reaction was quenched by careful addition of H2O
  3. customThe mixture was transferred to a separating funnel
  4. extractionextracted with DCM (50 ml)
  5. customThe organic portion was separated
  6. washwashed with 1M HCl, 1M NaOH, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customto give a brown solid

Sources & evidence

ORD record
ord-f8587036f3b341f48a88d15125c40d61
Source dataset
uspto-grants-2012_04
Patent number
US08163785B2

Reaction notes

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