Sodium Azide → HCID 86609126, compound

HRID 902338Notes

Reaction equation

HRID 902338 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:24]4[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:31])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C=O)C>[N:32]([CH2:12][C@H:13]1[CH:22]=[CH:21][C:20]2[C:15](=[C:16]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])[CH:17]=[C:18]([F:23])[CH:19]=2)[O:14]1)=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609115HCID 86609115, compound

Product 1

HCID 86609126HCID 86609126, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-(8-(2,6-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate prepared in Example 57, step 7 (500 mg, 1.0 mmol) and sodium azide (340 mg, 5.2 mmol) in anhydrous DMF (20 mL) was heated at 90° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (20 mL) and the resulting suspension stirred vigorously for 5 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Column chromatography on silica gel with 10–25% ethyl acetate in hexanes afforded 310 mg (85%) of (R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-6-fluoro-2H-chromene as a yellow oil. [α]D25=+282.1° (c=2.7 mg/0.7 MeOH); MS (EI) m/z 349. (M+).

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched by the addition of water (20 mL)
  3. customThe mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customthe organic phase separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2f63d476fa54a498c526e8de9f3edd2
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…