Pyridine → Methyl 3-[2,6-dichloro-4-(trifluoromethyl)phenylsulfonamido]thiophene-2-carboxylate

HRID 1925758Notes

Reaction equation

HRID 1925758 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[S:13](Cl)(=[O:15])=[O:14].[NH2:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25][CH3:26])=[O:24].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[S:13]([NH:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:15])=[O:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 27368692,6-Dichloro-4-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 67520512Methyl 3-[2,6-dichloro-4-(trifluoromethyl)phenylsulfonamido]thiophene-2-carboxylateYield 69.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Synthesized as described for 3 using 2,6-dichloro-4-(trifluoromethyl)benzene-1-sulfonyl chloride (2.5 g; 7.97 mmol), methyl 3-aminothiophene-2-carboxylate (1.14 g; 7.25 mmol), 4-dimethylaminopyridine (221.4 mg; 1.81 mmol), pyridine (11.81 mL; 145.0 mmol) and anhydrous dichloromethane (50 mL). Purification by automated silica gel chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution) afforded the title compound as a white solid (2.20 g).

Workup

  1. customSynthesized
  2. customPurification by automated silica gel chromatography (Biotage®)
  3. washeluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-6a68a64b3b484acb9b941d922a57dabf
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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