Hydrochloric Acid → Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate

HRID 894057Notes

Reaction equation

[Br-].[C:2]1([C:8]2[CH:25]=[CH:24][C:11]([C:12]([CH2:14][N+:15]3[CH:23]=[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][N:17]4[CH:16]=3)=[O:13])=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:36][CH2:37][CH3:38])(=[O:35])[C:33]#[CH:34].Cl>>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][N:15]1[C:14]([C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:25][CH:24]=2)=[CH:34][C:33]([C:32]([O:36][CH2:37][CH3:38])=[O:35])=[CH:16]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 11430Potassium Carbonate

HCID 12182Ethyl propiolate

HCID 128971102-(4-Phenylbenzoylmethyl)imidazo [3,4-a]pyridinium Bromide

Product 1

HCID 20401013Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylateYield 32.3%

Procedure

2-(4-Phenylbenzoylmethyl)imidazo[3,4-a]pyridinium bromide (16 g., 40 mmoles), potassium carbonate (22 g., 160 mmoles) and ethyl propiolate (6.4 ml., 48 mmoles) were combined according to the procedure of Example 69, stirred for approximately 16 hours at room temperature, then isolated and converted to hydrochloride according to the procedure of Example 69, to yield ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate (5.3 g., intermediate Rf on silica gel thin layer chromatography with ethyl acetate/5% acetic acid as eluant).

Workup

customisolated

Sources & evidence

ORD record: ord-a4e10ee4cfef440b887e2aa0419e7f2d
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04282242

Reaction notes

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