Tetrahydrofuran → 1-{5-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}ethane-1,2-diol

HRID 2281040Notes

Reaction equation

HRID 2281040 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[C:19]([F:26])=[N:20]C(C=C)=CC=4)=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.C[N+]1([O-])CC[O:31][CH2:30]C1.[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:36]=[CH:37][C:38]([CH:39]([OH:35])[CH2:30][OH:31])=[N:20][C:19]=4[F:26])=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 867119781-(cyclopropylmethyl)-5-(6-ethenyl-2-fluoropyridin-3-yl)-4-(trifluoromethyl)-1H-benzotriazole

Product 1

HCID 709782561-{5-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(Cyclopropylmethyl)-5-(6-ethenyl-2-fluoropyridin-3-yl)-4-(trifluoromethyl)-1H-benzotriazole (77 mg, 0.21 mmol) was dissolved in tetrahydrofuran (1.4 mL) and treated with osmium tetraoxide (270 uL, 0.043 mmol, 0.2 equiv) and N-methylmorpholine N-oxide (25 mg, 0.21 mmol, 1 equiv). After stirring at ambient temperature for 1.5 hours, the mixture was diluted with ethyl acetate (40 mL) and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. washwashed with sodium bicarbonate (2×30 mL, aqueous saturated)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3cd9793ba2ef407bb0977c587f9c97c0
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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