Azidotrimethylsilane → HCID 178487664, compound

HRID 332882Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([NH2:30])=O)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[Si]([N:35]=[N+:36]=[N-:37])(C)(C)C>COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=3[C:9]=2[O:19][C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]3[NH:30][N:37]=[N:36][N:35]=3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a microwave vial, (E)-3-(4-((2-(4-fluorophenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylamide (41 mg, 0.098 mmol) and Bu2SnO (2.433 mg, 9.77 mol) were suspended in DME (3 mL). The vial was charged with TMSN3 (0.013 mL, 0.098 mmol) and the reaction was heated for 60 min at 180° C. under microwave radiation. The reaction mixture was filtered to remove solids and concentrated onto silica gel. The crude material was purified by column chromatography (SiO2, 1-20% DCM/MeOH) to afford (E)-5-(4-((2-(4-fluorophenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-1H-tetrazole (31 mg, 0.070 mmol, 71.4% yield) as an orange solid. 1H NMR (400 MHz, CD3OD) δ ppm=3.78 (s, 3H) 6.80-6.91 (m, 3H) 6.96-7.07 (m, 3H) 7.19 (d, J=8.59 Hz, 1H) 7.34 (d, J=2.53 Hz, 1H) 7.35-7.52 (m, 3H) 7.58-7.74 (m, 2H).

Workup

filtrationThe reaction mixture was filtered
customto remove solids
concentrationconcentrated onto silica gel
customThe crude material was purified by column chromatography (SiO2, 1-20% DCM/MeOH)

Sources & evidence

ORD record: ord-ee980629f23742e69a35b937a604dee7
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877801B2

Reaction notes

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