Methanol → HCID 86673433, compound

HRID 2362402Notes

Reaction equation

HRID 2362402 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C@@H:8]2[C@@:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])([CH3:11])[O:9]2)[CH:7]=1.CO.[Cl-].[NH4+].[N-:24]=[N+:25]=[N-:26].[Na+]>O>[N:24]([C@H:8]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)[C@@:10]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[F:19])([OH:9])[CH3:11])=[N+:25]=[N-:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86673434HCID 86673434, compound

Product 1

HCID 86673433HCID 86673433, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Placed 3-bromo-5-((2R,3S)-3-(2,5-difluorophenyl)-3-methyloxiran-2-yl)pyridine (100 mg, 0.307 mmol), methanol (12 mL), water (1.500 mL), ammonium chloride (32.8 mg, 0.613 mmol), and sodium azide (120 mg, 1.840 mmol) in a microware tube and stirred for five minutes then sealed the tube and lowed it to a 110° C. oil bath for 18 hour. The reaction mixture was concentrate to provide a white solid to which was added 25 mL water then extracted it by ether (25 mL×3). Combined all ether layer, dried over magnesium sulfate, concentrated to afford clear wax which was purified via column chromatography (5% to 35% EtOAc/Hex) to provide (1R,2R)-1-azido-1-(5-bromopyridin-3-yl)-2-(2,5-difluorophenyl)propan-2-ol (96.2 mg, 0.248 mmol, 81% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.73 (d, J=2.1 Hz, 1H), 8.60 (d, J=1.8 Hz, 1H), 8.06 (t, J=1.8 Hz, 1H), 7.40 (ddd, J=9.8, 6.2, 3.2 Hz, 1H), 7.33-7.15 (m, 2H), 6.14 (s, 1H), 5.13 (s, 1H), 1.33 (d, J=0.9 Hz, 3H), Mass spec.: 371.1 (MH)+.

Workup

  1. customthen sealed the tube
  2. customto a 110° C.
  3. customfor 18 hour
  4. concentrationThe reaction mixture was concentrate
  5. customto provide a white solid to which
  6. extractionthen extracted it by ether (25 mL×3)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford clear wax which
  10. customwas purified via column chromatography (5% to 35% EtOAc/Hex)

Sources & evidence

ORD record
ord-c6371fb9dbc8401cad687d57a8acb95f
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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