Oxalyl chloride → N-(1-benzyl-1H-indazol-4-yl)-7-bromoimidazo[1,2-a]pyridine-3-carboxamide

HRID 706760Notes

Reaction equation

HRID 706760 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH2:20]([N:27]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([NH2:36])[C:30]=2[CH:29]=[N:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>ClCCl.CO.CN(C=O)C>[CH2:20]([N:27]1[C:35]2[C:30](=[C:31]([NH:36][C:11]([C:8]3[N:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]4=[N:10][CH:9]=3)=[O:13])[CH:32]=[CH:33][CH:34]=2)[CH:29]=[N:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 672614887-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67976233N-(1-benzyl-1H-indazol-4-yl)-7-bromoimidazo[1,2-a]pyridine-3-carboxamideYield 69.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (42 mg; 0.17 mmol) in dichloromethane (1 mL) was added oxalyl chloride (1.1 equivalents; 2M solution in dichloromethane) followed by a catalytic amount of DMF. The mixture was stirred in a sealed container stirred until effervescence stopped, venting occasionally to release gas. 1-Benzyl-1H-indazol-4-amine (Example 155, Steps A-B; 39 mg; 0.17 mmol) was added followed by diisopropylethylamine (2 equivalents). The mixture was stirred at ambient temperature for 2 days. The mixture was diluted with methanol and the solids were collected by filtration and washed twice with 2M aqueous sodium carbonate solution, water and ether. The solids were then dried to give the desired product as an off-white solid (53 mg).

Workup

  1. stirringstirred until effervescence
  2. stirringThe mixture was stirred at ambient temperature for 2 days
  3. filtrationthe solids were collected by filtration
  4. washwashed twice with 2M aqueous sodium carbonate solution, water and ether
  5. customThe solids were then dried

Sources & evidence

ORD record
ord-10a7111a4f8c4c7e8f8c50fb8bab184e
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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