Lithium Chloride → (4-Amino-3-trifluoromethyl-5-vinylbenzyl)carbamic Acid tert-butyl Ester

HRID 2358389Notes

Reaction equation

HRID 2358389 reaction equation
[Li+].[Cl-].[C:3]([O:7][C:8](=[O:23])[NH:9][CH2:10][C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:14]([NH2:21])=[C:13](I)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:24](C([Sn])=C(CCCC)CCCC)[CH2:25]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[C:3]([O:7][C:8](=[O:23])[NH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:24]=[CH2:25])[C:14]([NH2:21])=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 53438229Tri(butyl)vinyltinHCID 68456058(4-Amino-3-iodo-5-trifluoromethylbenzyl)carbamic acid tert-butyl ester

Product 1

HCID 68456886(4-Amino-3-trifluoromethyl-5-vinylbenzyl)carbamic Acid tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Pd(PPh3)4 (0.06 eq, 0.014 mmol, 16.64 mg) and LiCl (2.8 eq, 0.67 mmol, 28.49 mg) were added into DMF. (4-Amino-3-iodo-5-trifluoromethylbenzyl)carbamic acid tert-butyl ester (100 mg, 0.24 mmol) and tributylvinyltin (1.5 eq, 0.36 mmol, 105.37 μl) were added into the reaction mixture. The reaction mixture was stirred for 12 ha in reflux. The reaction mixture was purified according to step 4 of Example 8 to give a title product, yellow syrup (51.5 mg, 67.87%).

Workup

  1. temperaturein reflux
  2. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-1067bcd4ea6746a99d0107280fa5d252
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

Loading…