2-Iodobenzoic acid → (2-Iodo-phenyl)-[3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-methanone

HRID 1783787Notes

Reaction equation

HRID 1783787 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[Cl-].[Cl-].[Cl-].[Al+3].[N:15]1([CH2:21][CH2:22][C:23]2[N:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]3=[CH:25][N:24]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>ClCCCl>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:25]1[N:24]=[C:23]([CH2:22][CH2:21][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=12)=[O:6]

Participants

5

Reactant 3

HCID 69412-Iodobenzoic acidHCID 6451240Aluminum(III) ChlorideHCID 688300163-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine

Product 1

HCID 24948212(2-Iodo-phenyl)-[3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-methanoneYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 2-iodobenzoic acid (487 mg, 1.83 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (266 mg, 2.00 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (201 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixture was stirred at ambient temperature for 30 min. 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 (63 mg, 16%). %). 1H NMR (DMSO-d6) 8.54 (1H), 8.10 (1H), 7.92 (1H), 7.50 (1H), 7.41 (2H), 7.22 (1H), 7.10 (1H), 3.52 (4H), 3.18 (2H), 2.67 (2H), 2.40 (4H); m/z (M+H)=462.1.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 min.
  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-beccbf8452fd44c99978798d51b6cc77
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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