Benzyl azide → 2-((1-Benzyl-4-(tributylstannyl)-1H-1,2,3-triazol-5-yl)methyl)isoindoline-1,3-dione

HRID 1752553Notes

Reaction equation

[CH2:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])[C:2]#[CH:3].[CH2:15]([Sn:19]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])N(C)C)[CH2:16][CH2:17][CH3:18].[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CCCCCC>[CH2:31]([N:38]1[C:2]([CH2:1][N:4]2[C:8](=[O:9])[C:7]3[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]2=[O:14])=[C:3]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])[N:40]=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-Propargylphthalimide (2.35 g mg, 12.7 mmol) was added to 1,1,1-tributyl-N,N-dimethylstannanamine (4.23 mg, 12.7 mmol) in hexane (3.0 mL) and stirred in a sealed vial at 70° C. for 2 hours. The mixture was cooled to ambient temperature and the vial was stirred unsealed for 10 minutes. Benzyl azide (2.0 mL, 16.0 mmol) was added and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 10-50% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 609.3 (M+H)+.

Workup

temperatureThe mixture was cooled to ambient temperature
stirringthe vial was stirred unsealed for 10 minutes
temperatureheated to 130° C. overnight
customThe mixture was purified by silica gel chromatography
washeluting with a gradient of 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-9597f3295d344f678efbce61f42c2709
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163007B2

Reaction notes

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