Butyryl chloride → HCID 23649127, compound

HRID 1783772Notes

Reaction equation

HRID 1783772 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:11]1([C:21]2[N:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]3=[CH:23][N:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>ClCCl>[C:11]1([C:21]2[N:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]3=[C:23]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[N:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8855Butyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68831017HCID 68831017, compound

Product 1

HCID 23649127HCID 23649127, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of butyroylchloride (100 μL, 1.13 mmol) in dichloromethane (10 mL) was added aluminum trichloride (195 mg, 1.47 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-naphthalen-1-yl-imidazo[1,5-a]pyridine (276 mg, 1.13 mmol) in dichloromethane (5 mL) was added. The mixture was stirred for 30 min. at ambient temperature then washed with saturated aqueous sodium bicarbonate and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (25 mg, 8%). 1H NMR (DMSO-d6) δ 8.27 (1H), 8.19 (1H), 8.10 (1H), 7.95 (1H), 7.85 (1H), 7.68 (1H), 7.60 (2H), 7.55 (1H), 7.40 (1H), 6.95 (1H), 3.04 (2H), 1.70 (2H), 0.90 (3H); m/z (M+H)=315.2.

Workup

  1. stirringThe mixture was stirred for 30 min. at ambient temperature
  2. washthen washed with saturated aqueous sodium bicarbonate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-4e85b55bfbd644edb481e0577003a65c
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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