Lithium Chloride → (4-amino-3-vinylbenzyl)carbamic Acid t-butyl Ester

HRID 2358370Notes

Reaction equation

[Cl-].[Li+].[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13](I)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>CN(C=O)C>[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([CH:20]=[CH2:21])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

A 50 ml two-neck round bottom flask was filled with argon gas and the solution of tetrakis(triphenyl phosphine)palladium(0) (123.7 mg, 0.107 mmol, 0.06 eq.) and lithium chloride (211.9 mg, 4.998 mmol, 2.8 eq.) in DMF was put into the flask. To the solution was added (4-amino-3-iodobenzyl) carbamic acid t-butyl ester (621.4 mg, 1.875 mmol, 1 eq.) and tributylvinyltin (782.5 mg, 2.678 mmol, 1.5 eq.). The mixture solution was heated to 90° C. to reflux for one night. After confirming the completion of the reaction with TLC, the reaction solution was extracted with methylenechloride, washed with water and brine, dried over Na2SO4, filtered and evaporated. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=3/1) to yield brown liquid.

Workup

additionA 50 ml two-neck round bottom flask was filled with argon gas
temperatureto reflux for one night
customthe completion of the reaction with TLC
extractionthe reaction solution was extracted with methylenechloride
washwashed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=3/1)
customto yield brown liquid

Sources & evidence

ORD record: ord-7de3eef4449f49b7a80b05a4e32b4a68
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763657B2

Reaction notes

Loading…