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

HRID 1981009Notes

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) was 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-13266e2b13254ca1963359dbae33d4ff
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04511576

Reaction notes

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