Azidotrimethylsilane → HCID 136078974, compound

HRID 1472644Notes

Reaction equation

HRID 1472644 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, compound

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 IV-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
  5. customto afford Compound IV-11 (10 mg, 13.5%)

Sources & evidence

ORD record
ord-3cf50841c95944369bb94afe2e1e83c7
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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