Sodium Azide → HCID 58565360, compound

HRID 2175318Notes

Reaction equation

HRID 2175318 reaction equation
CS(O[CH:6]([C:8]1[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([Cl:17])[CH:11]=2)[CH3:7])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[N:25]([CH:6]([C:8]1[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([Cl:17])[CH:11]=2)[CH3:7])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86660479HCID 86660479, compound

Product 1

HCID 58565360HCID 58565360, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude 1-[6-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]ethyl methanesulfonate in N,N-dimethylformamide (1 mL) was added sodium azide (57 mg, 0.88 mmol). The reaction was stirred at room temperature for 2 hours, quenched with water, and then extracted with EtOAc. The extracts were combined, washed with brine, dried over MgSO4 and concentrated to give the desired azide (55 mg), which was used directly in the next step. LCMS calculated for C16H12ClFN (M-N3)+: m/z=272.1. Found: 271.9.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83806de694884e1681d38d92d6591e5b
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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