Sodium Azide → HCID 58565371, compound

HRID 2175328Notes

Reaction equation

HRID 2175328 reaction equation
CS(O[CH:6]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:7])(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([CH:6]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:7])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866604801H-Indole-2-methanol, 1-(3-fluorophenyl)-α-methyl-, 2-methanesulfonate

Product 1

HCID 58565371HCID 58565371, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethyl methanesulfonate in N,N-dimethylformamide (5 mL) was added sodium azide (0.20 g, 3.0 mmol). The reaction was stirred at room temperature for 2 hr, quenched with water, and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated and purified on silica gel (eluting with 0-30% EtOAc in hexane) to give the desired product (0.14 g, 49%). LCMS calculated for C16H13FN(M-N3)+: m/z=238.1. Found: 238.1.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-31a891857b264d4eae5d883f77deb276
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

Loading…