Azidotrimethylsilane → HCID 136078974, compound

HRID 55789Notes

Reaction equation

HRID 55789 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH:3]=1.[Si]([N:25]=[N+:26]=[N-:27])(C)(C)C>C1(C)C=CC=CC=1>[N:18]1[NH:25][N:26]=[N:27][C:17]=1[C:16]1[CH:19]=[CH:20][C:13]([C:4]2[CH:3]=[C:2]([Cl:1])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 66980076HCID 66980076, compound

Product 1

HCID 136078974HCID 136078974, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Followed Scheme 4, route A. To a solution of 4-(4-chloro-6-hydroxyquinolin-2-yl)benzonitrile (65 mg, 0.23 mmol) in toluene (2 mL), was added TMSN3 (455 mg, 4.18 mmol) and Bu2SnO (15 mg, 0.069 mmol) at room temperature. The mixture was heated to reflux overnight. The volatiles were removed under reduced pressure. The residue was purified by prep-HPLC to afford Compound 11 (10 mg, 13.5%). 1H NMR (MeOD-d4, 500 MHz): δ 8.34 (d, J=8.5 Hz, 2H), 8.21 (s, 1H), 8.19 (s, 2H), 8.07 (d, J=9.0 Hz, 1H), 7.51 (d, J=2.5 Hz, 1H), 7.47 (dd, J=2.5 Hz, J=9.5 Hz, 1H). MS (ESI): m/z 324.0 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-71589b8db8f0403c83f64c4dc6b5cbd9
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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