Diazomethane → HCID 19605521, compound

HRID 1603584Notes

Reaction equation

HRID 1603584 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[C:6]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[N:5]=1)([CH3:3])=[CH2:2].[N+](=[CH2:27])=[N-]>C(OCC)C.C(O)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:2][C:1]1([C:4]2[CH:9]=[C:8]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)(=[O:11])=[O:12])[CH:7]=[C:6]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[N:5]=2)[CH2:27][CH2:3]1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 196055234-(2-Isopropenyl-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine

Product 1

HCID 19605521HCID 19605521, compoundYield 71%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

0.164 g (0.00048 Mol) 4-(2-Isopropenyl-6-pyrrolidin-1-yl-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 0.136 g (71%) of 4-[2-(1-Methyl-cyclopropyl)-6-pyrrolidin-1-yl-pyridine-4-sulfonyl]-phenylamine as pale yellow cristals; mp.: 235-236° C. (dec.).

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-24cfe0b830354b28b74f5b9080097c8d
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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