Azidotrimethylsilane → HCID 178515315, compound

HRID 410013Notes

Reaction equation

HRID 410013 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)=[C:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[Si]([N:29]=[N+:30]=[N-:31])(C)(C)C>C1(C)C=CC=CC=1>[NH:29]1[C:20]([C:19]2[CH:22]=[CH:23][C:16]([C:7]3[C:6](=[O:24])[C:5]4[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=4)[O:9][C:8]=3[C:12]([F:15])([F:13])[F:14])=[CH:17][CH:18]=2)=[N:21][N:31]=[N:30]1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 67366080HCID 67366080, compound

Product 1

HCID 178515315HCID 178515315, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(7-hydroxy-4-oxo-2-(trifluoromethyl)-4H-chromen-3-yl)benzonitrile (50 mg, 0.15 mmol) in toluene (2 ml), was added TMSN3 (296 mg, 2.72 mmol) and Bu2SnO (10 mg, 0.045 mmol) at room temperature. The mixture was refluxed overnight. The volatiles were removed under reduced pressure. The residue was purified by prep-HPLC to afford desired product in Example 1 as a yellow powder (19.4 mg, 34.6%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-0839e22ad6cc479f863f63cec7ef7d0e
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

Loading…