Triethylamine → HCID 59655926, compound

HRID 2054366Notes

Reaction equation

HRID 2054366 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([Sn:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9].Cl[S:15]([CH3:18])(=[O:17])=[O:16].CCN(CC)CC.CCOC(C)=O.O>C(Cl)Cl>[CH3:18][S:15]([NH:1][CH2:2][C:3]1[CH:4]=[C:5]([Sn:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22728543Water ethylacetateHCID 59655900HCID 59655900, compound

Product 1

HCID 59655926HCID 59655926, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-aminomethyl-4-fluoro-1-trimethylstannylbenzene (507.9 mg, 1.76 mmol), ClSO2Me (180.9 μL, 2.29 mmol) and NEt3 (492 μL, 3.52 mmol) was stirred at room temperature in CH2Cl2 (18 mL). After 3 h, extractive EtOAc/H2O workup followed by flash chromatography (EtOAc/Hexanes, 20:80) provided the title compound (342 mg, 53%) as an oil. 1H NMR (CDCl3, 400 MHz.

Sources & evidence

ORD record
ord-0a0dcc4400ae49d49ae378404cd49edd
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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