Dichloromethane → HCID 86673358, compound

HRID 518010Notes

Reaction equation

HRID 518010 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]3[N:19]=[N:20][N:21]([CH3:22])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:23]([F:26])([F:25])[F:24].C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O.C(OCC)(=O)C>[CH3:22][N:21]1[C:13]2[CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH:2]=[O:1])=[C:6]([C:23]([F:25])([F:24])[F:26])[CH:7]=3)[N:16]=[C:15]([C:17]#[N:18])[C:14]=2[N:19]=[N:20]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 67294126HCID 67294126, compound

Product 1

HCID 86673358HCID 86673358, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6-(4-(3-hydroxypropyl)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.65 g) in DMSO (10 ml) was added the DCM solution of Dess-Martin (15%, w/w) (10 ml). The mixture was stirred at rt for 2 hours. After diluting with ethyl acetate (150 ml), the mixture was washed with water (20 ml×4), brine (20 ml), dried over sodium sulphate, solvent removed under reduced pressure. The residue was then dissolved in ethyl acetate (20 ml). After standing overnight, precipitate was then filtered off, filtrate concentrated to give methyl-6-(4-(3-oxopropyl)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (620 mg). 1H NMR (CDCl3) δ: 9.88 (s, 1H), 8.36 (s, 1H), 8.26 (d, 1H), 8.05 (s, 1H), 7.55 (d, 1H), 4.46 (s, 3H), 3.22 (t, 2H), 2.86 (t, 2H). MS m/z 360 (M+H).

Workup

  1. washthe mixture was washed with water (20 ml×4), brine (20 ml)
  2. dry with materialdried over sodium sulphate, solvent
  3. customremoved under reduced pressure
  4. dissolutionThe residue was then dissolved in ethyl acetate (20 ml)
  5. waitAfter standing overnight
  6. filtrationprecipitate was then filtered off
  7. concentrationfiltrate concentrated

Sources & evidence

ORD record
ord-adc2d7c87820414bb6057ad3f8312c7c
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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