Diazomethane → HCID 19605499, compound

HRID 1603569Notes

Reaction equation

HRID 1603569 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:9]=[C:8]([CH:22]=[CH2:23])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:26])=[N-]>C(OCC)C.C(O)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:22]1([C:8]2[CH:9]=[C:10]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:11]=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=2)[CH2:26][CH2:23]1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 19605526HCID 19605526, compound

Product 1

HCID 19605499HCID 19605499, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

0.165 g (0.0005 Mol) 4-(2-Pyrrolidin-1-yl-6-vinyl-pyridine-4-sulfonyl)-phenylamine were dissolved in ethyl ether (100 ml) and cooled to 0° C. A solution of diazomethane in ethyl ether (30 ml) was carefully added. Upon addition of a catalytic amount of Pd(OAc)2 gas evolution started. The reaction mixture was allowed to warm to ambient temperature and stirred for 30 min. After addition of a few drops of acetic acid the solvent was evaporated and the residue chromatographed on SiO2 with ethyl acetate hexane 1:2. It was obtained 0.149 g (87%) of 4-(2-cyclopropyl-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine as bright yellow cristals; mp.: 216-218° C.

Workup

  1. temperatureto warm to ambient temperature
  2. customwas evaporated
  3. customthe residue chromatographed on SiO2 with ethyl acetate hexane 1:2

Sources & evidence

ORD record
ord-32919eb7de0b4f4ab55d7507c0fa5e8a
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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