Ethyl Acetate → 2-(2-Cyclopropylethynyl)-5-methylsulfonylaniline

HRID 518509Notes

Reaction equation

HRID 518509 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.[C:15]([CH:17]1[CH2:19][CH2:18]1)#[CH:16].C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>CC#N.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH:17]1([C:15]#[C:16][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=2[NH2:12])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8857Ethyl Acetate2×HCID 11430Potassium CarbonateHCID 138823CyclopropylacetyleneHCID 20603662-Bromo-5-methylsulfonylnitrobenzene

Product 1

HCID 1180214862-(2-Cyclopropylethynyl)-5-methylsulfonylanilineYield 95.1%

Reagents, catalysts & solvents 2

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 6342AcetonitrileSolvent

Procedure

bromo-4-methylsulfonyl-2-nitrobenzene (1.5 g, 5.36 mmol), ethynylcyclopropane (0.7 g, 10.72 mmol), K2CO3 (1.5 g, 10.72 mmol) in CH3CN (30 ml), Pd(ACN)2Cl2 (55.5 mg, 0.21 mmol) and X-phos (128 mg, 0.27 mmol) under N2 were heated at 45° C. for 3 h. EA extractive work up and preparative TLC (PE: EtOAc=5:1) gave the title compound (1.2 g).

Sources & evidence

ORD record
ord-a4a8bcbbcf0e4fdfb551da0ff3df3f54
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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