Toluene → HCID 178489274、化合物

反応式

[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([C:25]#[N:26])=[N:23]2)=[CH:18][CH:17]=1.C1(C)C=CC=CC=1.C([Sn](CCCC)=O)CCC>>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([C:25]3[NH:26][N:3]=[N:2][N:1]=3)=[N:23]2)=[CH:18][CH:17]=1

参加物

反応物 4

HCID 1140Toluene

HCID 61221Dibutyltin oxide

HCID 78378Azidotrimethylsilane

HCID 667124197-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile

生成物 1

HCID 178489274HCID 178489274、化合物

反応条件

温度: 90 °C

実験手順

Azidotrimethylsilane (0.250 mL, 1.88 mmol) was added to 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (48.0 mg, 0.192 mmol) in Toluene (4.0 mL, 38 mmol) and Dibutyloxostannane (50.0 mg, 0.201 mmol) and heat at 90° C. for 4 h. Cool and conc. in vacuo, then purify by prep HPLC. The lyophilate was dissolved in MeOH, loaded onto a Phenomenex sulfonic acid resin, which was washed with MeOH and then the product eluted as the free base with 2M NH3 in MeOH. Conc. and reconc. from DCM afforded 7-(2-Methoxy-phenyl)-2-(1H-tetrazol-5-yl)-pyrrolo[2,1-f][1,2,4]triazine as a yellow film. LCMS (HPLC): 294 (M+H); 1H-NMR (DMSO-d6): 9.25 (s, 1H), 7.83 (m, 1H), 7.47 (m, 1H), 7.23 (m, 2H), 7.11 (m, 3H), 3.83 (s, 3H).