Tin tetrachloride → 4-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 456667Notes

Reaction equation

HRID 456667 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][CH:7]=1)=[O:5])[CH3:2].N1C=CC(C(O)=O)=C1.[Cl:19][C:20]1[N:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:22]([C:21]2[C:20]([Cl:19])=[N:28][CH:27]=[CH:26][CH:25]=2)=[O:23])=[CH:9][NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 101030Pyrrole-3-carboxylic acidHCID 27745412-Chloronicotinoyl chlorideHCID 13070719Ethyl 1H-pyrrole-3-carboxylate

Product 1

HCID 865922474-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl esterYield 10%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1H-pyrrole-3-carboxylic acid ethyl ester (2 g, 14.4 mmol) (synthesized from 1H-pyrrole-3-carboxylic acid suing the same procedure as in Example 30) and 2-chloronicotinoyl chloride (4.4 mg, 25 mmol) in dry benzene (10 mL) at 0° C. was added dropwise a solution of tin (IV) chloride (0.7 g) in dry benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for overnight. The reaction was diluted with ethyl acetate, washed with brine and concentrated. The residue was purified on a silica gel column to give 402 mg (10%) of 4-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-carboxylic acid ethyl ester.

Workup

  1. washwashed with brine
  2. concentrationconcentrated
  3. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-bfa2f47f4c5044d7815ce362d53ff94b
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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