Oxalyl chloride → HCID 47364487, compound

HRID 1027272Notes

Reaction equation

HRID 1027272 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][N:20]1[CH:24]=[C:23]([CH2:25][NH2:26])[CH:22]=[N:21]1>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:26][CH2:25][C:23]1[CH:22]=[N:21][N:20]([CH3:19])[CH:24]=1)=[O:7]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 668363-Bromo-4-methoxybenzoic acidHCID 671225(1-methyl-1H-pyrazol-4-yl)methanamine

Product 1

HCID 47364487HCID 47364487, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL round bottom flask containing 3-bromo-4-methoxybenzoic acid (500 mg, 2.16 mmol) and DCM (5 mL) was added oxalyl chloride (0.23 mL, 2.60 mmol) and DMF (0.1 mL, 0.13 mmol). The reaction mixture was stirred at RT for one hour and concentrated in vacuo. The resulting colorless oil was taken up in DCM (2.5 mL) and added to a mixture of (1-methyl-1H-pyrazol-4-yl)methanamine (241 mg, 2.16 mmol), TEA (0.60 mL, 4.33 mmol) and DCM (2.5 mL) at 0° C. The reaction mixture was stirred at RT for 0.5 hours then concentrated in vacuo. The crude material was purified by silica gel chromatography (0-10% MeOH in DCM) to afford 3-bromo-4-methoxy-N-((1-methyl-1H-pyrazol-4-yl)methyl)benzamide (702 mg) MS [M+H+]=325.9.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe reaction mixture was stirred at RT for 0.5 hours
  3. concentrationthen concentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-4adf2f6f5e9b43aebc42975590b9b611
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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