Azidotrimethylsilane → HCID 178419993, compound

HRID 33930Notes

Reaction equation

HRID 33930 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.[N:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1>>[N:8]1[CH:9]=[CH:10][C:11]([C:14]2[NH:7][N:6]=[N:5][C:15]=2[C:16]2[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)=[CH:32][CH:33]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 597975072-((4-(2-(Pyridin-4-yl)ethynyl)phenoxy)methyl)quinoline

Product 1

HCID 178419993HCID 178419993, compoundYield 85.2%

Conditions

Temperature
150 °C

Procedure

Trimethylsilylazide (730 mg, 6.4 mmol) and 2-((4-(2-(pyridin-4-yl)ethynyl)phenoxy)methyl)quinoline (360 mg) were combined in a screw cap sealed tube and heated behind a safety shield in a 150° C. bath for 72 h. The mixture was concentrated and the yellow residue triturated with ether (2×10 mL) leaving a yellow solid (346 mg) which was chromatographed on silica eluted with a gradient of 0.5%-2% methanol in dichloromethane giving a yellow solid (210 mg,52%). 1H NMR (CDCl3 with a drop of CD3OD, 400 mHz) δ 8.54 (d, 2H, J=6.2 Hz), 8.23 (d, 1H, J=8.7 Hz), 8.07 (d, 1H, J=8.7 Hz), 7.84 (d, 1H, J=7.9 Hz), 7.74 (ddd, 1H, J=8.4, 7, 1Hz), 7.69 (d, 1H, J=8.7 Hz), 7.63 (d, 2H, J=6.2 Hz), 7.56 (ddd, 1H), 7.41 (m, 2H), 7.09 (m, 2H), 5.41 (s, 2H). MS (AP+) m/e 380 (MH+).

Workup

  1. customcap
  2. customsealed tube
  3. concentrationThe mixture was concentrated
  4. customthe yellow residue triturated with ether (2×10 mL)

Sources & evidence

ORD record
ord-8d077caaf34e40d7bcd6ce5392da874d
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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