Azidotrimethylsilane → HCID 178515315, compound

HRID 714494Notes

Reaction equation

HRID 714494 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-dda267aa03c54783b7980c081f9af158
Source dataset
uspto-grants-2015_11
Patent number
US09187447B2

Reaction notes

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