Tin tetrachloride → ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-2-carboxylate

HRID 456654

Reaction equation

HRID 456654 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[Cl:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10].[CH2:16]([O:18][C:19]([C:21]1[NH:22][CH:23]=[CH:24][CH:25]=1)=[O:20])[CH3:17]>C1C=CC=CC=1>[CH2:16]([O:18][C:19]([C:21]1[NH:22][C:23]([C:9]([C:8]2[C:7]([Cl:6])=[N:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:24][CH:25]=1)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 76853860ethyl 5-(2-chloronicotinoyl)-1H-pyrrole-2-carboxylateYield 104.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of tin (IV) chloride (3.72 g, 5 mmol) in benzene (10 mL) was added dropwise to a mixture of 2-chloronicotinoyl chloride (2.02 g, 11 mmol) and 1H-pyrrole-2-carboxylic acid ethyl ester (0.73 g; prepared as discussed below) in dry benzene (12 mL) at 0° C. The reaction was allowed to warm up slowly to room temperature and stirred 4 hours. The reaction was concentrated, the residue was dissolved in ethyl acetate and washed with brine, dried and concentrated to give 1.53 g of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ethyl ester as a brown solid.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d38964236d2c4a69aec393fdd3a027ec
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Linked notes

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