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 1671312Notes

Reaction equation

HRID 1671312 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-crf38

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 (Ex. 6.12) (100 mg, 0.285 mmol) is dissolved in dry DCM (5 ml). The contents are flushed with N2 and to this solution is added boron tribromide (1.423 ml, 1.423 mmol) dropwise at RT. After approximately 30 mins, the reaction is quenched by careful addition of H2O. The mixture is transferred to a separating funnel and extracted with DCM (50 ml). The organic portion is separated and washed with 1M HCl, 1M NaOH, brine, dried (MgSO4) and evaporated in vacuo to give a brown solid. Trituration with EtOAc affords the title compound as an off white solid. MS m/z 338.2 [M+H]+; 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. customThe contents are flushed with N2 and to this solution
  2. customthe reaction is quenched by careful addition of H2O
  3. customThe mixture is transferred to a separating funnel
  4. extractionextracted with DCM (50 ml)
  5. customThe organic portion is 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-13bede565d47486aa1a0d802f941d410
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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