Bromomethyl 4-methoxyphenyl ketone → Ethyl 2-amino-5-(4-methoxyphenyl)-1H-pyrrole-3-carboxylate

HRID 369851Notes

Reaction equation

HRID 369851 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH2:6][C:7](=[NH:9])[NH2:8])[CH3:3].C([O-])C.[Na+].[CH3:15][O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21](=O)[CH2:22]Br)=[CH:19][CH:18]=1>C(O)C>[NH2:9][C:7]1[NH:8][C:21]([C:20]2[CH:25]=[CH:26][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[CH:22][C:6]=1[C:5]([O:4][CH2:2][CH3:3])=[O:10]

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 2723922Sodium ethoxideHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Product 1

HCID 23282706Ethyl 2-amino-5-(4-methoxyphenyl)-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to Step 8.1, 1.67 g (10 mmol) of 2-amidino-acetic acid ethyl ester hydro-chloride in 20 ml of abs. ethanol are reacted with 716 mg (10 mmol) of sodium ethanolate and 1.145 g (5.0 mmol) of 4-methoxy-phenacyl bromide (Fluka; Buchs/Switzerland) to form the title compound; m.p. 141-142° C.; TLC-Rf =0.4 (hexane/ethyl acetate [1:1]); FAB-MS: (M+H)+ =261.

Sources & evidence

ORD record
ord-a60f0bc826f24487b98c316006e98e7b
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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