Azido(trimethyl)stannane → HCID 178437421, compound

HRID 1742416Notes

Reaction equation

[CH2:1]([C:3]1[N:13]([CH:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]#[N:26])=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C[Sn]([N:35]=[N+:36]=[N-:37])(C)C>C1(C)C(C)=CC=CC=1>[CH2:1]([C:3]1[N:13]([CH:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]4[NH:37][N:36]=[N:35][N:26]=4)=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of 2-[1-(2-ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-yl)-indan-5-yl]-benzonitrile (100 mg, 0.26 mmol) and trimethyltin azide (110 mg, 0.51 mmol) in xylene (3.0 mL) was heated under reflux for 48 hours. The reaction mixture was cooled to 23° C. and the solvent was removed in vacuo. The crude residue was chromatographed on SiO2 -gel using 10% MeOH/CH2Cl2 to afford 45 mg of the tetrazole, mp-181 ° C. 1H NMR (250 MHz, d6 -DMSO): d 7.64 (m, 1 H), 7.53 (m, 1 H), 7.15 (s, 1 H), 6.91 (s, 1 H), 6.80 (d, 1 H), 6.70 (d, 1 H), 6.48 (m, 1 H), 3.04 (m,2 H), 2.68 (2H, m) 2.49 (s, 3 H), 2.42 (s, 3 H), 1.25 (t, 3 H); MS (M+): 435

Workup

temperaturewas heated
temperatureunder reflux for 48 hours
customthe solvent was removed in vacuo
customThe crude residue was chromatographed on SiO2

Sources & evidence

ORD record: ord-8aaa05863aee44d6bb19b0cf16cb6954
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05338740

Reaction notes

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