N-bromobutanimide → 5-Bromomethyl-4-chloro-3-cyano-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester

HRID 2183479Notes

Reaction equation

HRID 2183479 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].C1C(=O)N([Br:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:18][Br:26])=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21025099HCID 21025099, compound

Product 1

HCID 207916315-Bromomethyl-4-chloro-3-cyano-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl EsterYield 99.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
77 °C

Procedure

A suspension of compound 1D (79 mg, 0.30 mmol), NBS (59 mg, 0.33 mmol) and benzoyl peroxide (5 mg, 0.02 mmol) in CCl4 (2 mL) was heated at 77° C. for 3 hours. After cooling to room temperature, the reaction was purified by a short silica gel column (eluted with CH2Cl2) to give compound 16A as a yellow solid (102 mg, 99%). B. 4-Chloro-3-cyano-5-hydroxymethyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester (16B)

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was purified by a short silica gel column (eluted with CH2Cl2)

Sources & evidence

ORD record
ord-a7a783b33514403490cee7be8a358d44
Source dataset
uspto-grants-2005_05
Patent number
US06900208B2

Reaction notes

Loading…