Nitrogen → 3-Azido-2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)propan-2-ol

HRID 63262Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([F:26])([F:25])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][N:14]=2)[CH2:11][O:10]1.[Cl-].[NH4+].[N-:29]=[N+:30]=[N-:31].[Na+].N#N>CO>[N:29]([CH2:11][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:10])[C:12]([F:26])([F:25])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][N:14]=1)=[N+:30]=[N-:31]

Participants

Conditions

Temperature: 50 °C

Procedure

To a magnetically stirred mixture of 2-((2-(2,4-difluorophenyl)oxiran-2-yl)difluoromethyl)-5-(2,2,2-trifluoroethoxy)pyridine (775 mg, 2.033 mmol) and ammonium chloride (326 mg, 6.10 mmol) in MeOH (6.776 mL) was added sodium azide (396 mg, 6.10 mmol) in a 20 mL vial under a N2 atmosphere. The reaction mixture was stirred at 50° C. for 16 h. The reaction was cooled to rt, then volatiles were removed under a gentle stream of N2. Et2O was added to the resulting residue and stirred rapidly for 5 min, then filtered to remove solids. The volatiles were removed by rotary evaporation and the resulting oil was carried on without further purification.

Workup

temperatureThe reaction was cooled to rt
customvolatiles were removed under a gentle stream of N2
additionEt2O was added to the resulting residue
stirringstirred rapidly for 5 min
filtrationfiltered
customto remove solids
customThe volatiles were removed by rotary evaporation
customthe resulting oil was carried on without further purification

Sources & evidence

ORD record: ord-ecc207108825452b85c91e286fa0594d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447073B2

Reaction notes

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