Water → 5-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridine-2-carbaldehyde

HRID 2281041Notes

Reaction equation

HRID 2281041 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([CH:25]([OH:28])CO)=[N:22][C:23]=4[F:24])=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.O.I([O-])(=O)(=O)=O.[Na+]>C(#N)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([CH:25]=[O:28])=[N:22][C:23]=4[F:24])=[C:13]([C:14]([F:16])([F:15])[F:17])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 709782561-{5-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}ethane-1,2-diol

Product 1

HCID 867119795-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-{5-[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}ethane-1,2-diol (32 mg, 0.081 mmol) was dissolved in acetonitrile (1 ml) and deionized water (0.5 mL), cooled to 0° C. and treated with sodium periodate (19 mg, 0.089 mmol, 1.1 equiv). The ice bath was removed and the mixture was warmed to ambient temperature and stirred for 1 hour, which was diluted with ethyl acetate (30 mL) and washed with sodium bicarbonate (2×15 mL, aqueous saturated). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. customThe ice bath was removed
  2. additionwhich was diluted with ethyl acetate (30 mL)
  3. washwashed with sodium bicarbonate (2×15 mL, aqueous saturated)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6da89be33f3442d9adb3107cc63f44d
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

Loading…