2,4-Dimethylbenzoyl chloride → HCID 58896488, compound

HRID 2235541Notes

Reaction equation

HRID 2235541 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[N:5]2[CH:17]=1.[Li]C(C)(C)C.[CH3:23][C:24]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C1COCC1>[CH3:23][C:24]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:25]=1[C:26]([C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[N:5]2[CH:17]=1)=[O:27]

Participants

5

Reactant 3

HCID 1408672,4-Dimethylbenzoyl chlorideHCID 685819902-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amineHCID 178418306HCID 178418306, compound

Product 1

HCID 58896488HCID 58896488, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amine (prepared in example 61) (0.136 g, 0.46 mmol) was dissolved in THF (1 mL). The solution was cooled to −78° C. t-BuLi (1.7M, 0.57 mL, 0.96 mmol) was added dropwise and the solution stirred for 1 hr. at −78° C. 2,4-Dimethylbenzoyl chloride (0.097 g, 0.57 mmol) diluted in 0.5 mL THF was added to the reaction mixture. After 0.5 hr, the solution was quenched with water and warmed to room temperature. Extraction occurred with EtOAc and the organic layer was dried over magnesium sulfate and concentrated. Flash chromatography (30-40% EtOAc/hexanes) gave the title compound. 0.039 g obtained (24% yield).

Workup

  1. additionwas added dropwise
  2. customat −78° C
  3. additionwas added to the reaction mixture
  4. waitAfter 0.5 hr
  5. customthe solution was quenched with water
  6. extractionExtraction
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7827deb42bef4841a91038a3328e0bf5
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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