Pyridine → Methyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-sulfonamido)thiophene-2-carboxylate

HRID 1925756Notes

Reaction equation

HRID 1925756 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14](Cl)(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2.[NH2:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([S:14]([NH:19][C:20]3[CH:24]=[CH:23][S:22][C:21]=3[C:25]([O:27][CH3:28])=[O:26])(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 27954675,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenesulfonyl chloride

Product 1

HCID 67520696Methyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-sulfonamido)thiophene-2-carboxylateYield 50.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Synthesized as described for 3 using 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride (500.0 mg; 1.74 mmol), methyl 3-aminothiophene-2-carboxylate (301.4 mg; 1.91 mmol), 4-dimethylaminopyridine (53.1 mg; 0.44 mmol), pyridine (1.40 mL; 17.4 mmol) and anhydrous dichloromethane (200 mL). The crude residue was purified by automated silica gel chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 25% v/v over 350 mL gradient elution) to yield the title compound as a white solid (359 mg).

Workup

  1. customSynthesized
  2. customThe crude residue was purified by automated silica gel chromatography (Biotage®)
  3. washeluting with ethyl acetate/hexanes (0 to 25% v/v over 350 mL gradient elution)

Sources & evidence

ORD record
ord-92e3ab7097914666814b4f34a63c383e
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

Loading…