Azidotrimethylsilane → HCID 136078974, compound

HRID 628861Notes

Reaction equation

HRID 628861 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-2d1f643983c34bcdaf9739335794d9ff
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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