Dibutyltin oxide → HCID 66607718, compound

HRID 1810591Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:35])[N:10]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[C:28]([CH2:30][C:31]#[N:32])[CH:27]=[CH:26][C:25]=1[O:33][CH3:34])[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:35])[N:10]([CH2:11][CH3:12])[CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[C:28]([CH2:30][C:31]2[N:36]=[N:37][NH:38][N:32]=2)[CH:27]=[CH:26][C:25]=1[O:33][CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

(5′-Cyanomethyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-ethyl-carbamic acid benzyl ester (0.209 g, 0.43 mmol), azidotrimethylsilane (0.07 mL, 0.52 mmol), and dibutyltin oxide (0.015 g, 0.04 mmol) were combined in toluene (2.1 mL) and stirred at 110° C. overnight Analytical LCMS indicated that the reaction wasn't proceeding, so additional azidotrimethylsilane (0.04 mL, 0.26 mmol), and dibutyltin oxide (catalytic) was added, and the reaction was stirred at 100° C. overnight. The mixture was cooled to room temperature and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound. M+H is 526.

Workup

additionwas added
stirringthe reaction was stirred at 100° C. overnight
temperatureThe mixture was cooled to room temperature
concentrationconcentrated
customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-215ffec7c4e8444bab75aa21e1d18dca
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362044B2

Reaction notes

Loading…