Potassium Carbonate → HCID 70393619, compound

HRID 620083Notes

Reaction equation

HRID 620083 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1.[CH3:22][O:23][C:24]([C:26]1[CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)[C:30]([C:41]([OH:43])=[O:42])=[C:29]([CH3:44])[NH:28][C:27]=1[CH3:45])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:22][O:23][C:24]([C:26]1[CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-:40])=[O:39])[CH:33]=2)[C:30]([C:41]([O:43][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=2)=[O:42])=[C:29]([CH3:44])[NH:28][C:27]=1[CH3:45])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 21248436HCID 21248436, compound

Product 1

HCID 70393619HCID 70393619, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8.7 g (24 mmol) of the bromine derivative obtained in step 2b), 8.0 g (24 mmol) of 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridine-dicarboxylic acid monomethyl ester and 6.6 g (48 mmol) of potassium carbonate are heated at boiling in 100 ml of acetonitrile for 20 hours while stirring and under reflux. Working up analogously to Example 1c yields 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-tertiary butoxycarbonylaminoethoxy)-phenoxy]-ethyl}-ester 5-methyl ester, which is used in the following step without being purified further.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-c967dfcf1d914e33af38ae9d37cb9995
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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