Oxalyl chloride → N-(1-benzyl-1H-indazol-4-yl)-6-bromoimidazo[1,2-a]pyridine-3-carboxamide

HRID 706754Notes

Reaction equation

HRID 706754 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=2)[CH:7]=1.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[CH2:29]([N:36]1[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([NH2:45])[C:39]=2[CH:38]=[N:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CCOCC.CN(C=O)C>[CH2:29]([N:36]1[C:44]2[C:39](=[C:40]([NH:45][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[O:13])[CH:41]=[CH:42][CH:43]=2)[CH:38]=[N:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531Diisopropylethylamine2×HCID 213273171-benzyl-1H-indazol-4-amineHCID 220319126-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 67976196N-(1-benzyl-1H-indazol-4-yl)-6-bromoimidazo[1,2-a]pyridine-3-carboxamideYield 47.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid (200 mg; 0.83 mmol) was suspended in methylene chloride (2 mL) with a catalytic (0.005 mL) amount of DMF. A solution of oxalyl chloride (0.913 mmol; 2M solution on dichloromethane) was added. The mixture was stirred in a sealed vial (with occasional venting to release gas) until effervescence ceased (about 30 minutes). A white suspension resulted. Diisopropylethylamine (188 μL; 1.08 mmol) was added. A clear solution resulted. 1-Benzyl-1H-indazol-4-amine (185 mg; 0.83 mmol) was added as a solution in methylene chloride followed by addition of further diisopropylethylamine (188 μL). The mixture was stirred at ambient temperature for 24 hours. A suspension resulted. The mixture was diluted with ether (10 mL) and the solids were collected by filtration. The filter pad was washed with ether and water and the solids were dried under vacuum to provide the desired product as a white solid (175 mg). MS (APCI) positive scan, m/z=446, 449 (M+H).

Workup

  1. custom(about 30 minutes)
  2. customA white suspension resulted
  3. customA clear solution resulted
  4. stirringThe mixture was stirred at ambient temperature for 24 hours
  5. customA suspension resulted
  6. filtrationthe solids were collected by filtration
  7. washThe filter pad was washed with ether and water
  8. customthe solids were dried under vacuum

Sources & evidence

ORD record
ord-e0b35cca69904d7b92d53301d49426ca
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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