669091-15-0 → 2-(3-Methoxy-4-pyridin-2-ylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

HRID 2213093Notes

Reaction equation

HRID 2213093 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]3[CH:23]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3[CH:23]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 10380127669091-15-0

Product 1

HCID 102670962-(3-Methoxy-4-pyridin-2-ylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(3-methoxy-4-pyridin-2-ylphenyl)imidazo[1,2-a]pyridine (40 mg, 0.13 mmol) in methanol (2 mL) was treated with Pd/C (8 mg of 10%) and stirred vigorously under an atmosphere of hydrogen gas for 3 days. The reaction mixture was filtered through a pad of celite, and the filtrate was concentrated to afford the desired 2-(3-methoxy-4-pyridin-2-ylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine as a yellow solid. 1H NMR (CD3OD, 300 MHz) δ 8.88 (d, 1H), 8.69 (m, 1H), 8.35 (d, 1H), 8.09 (m, 2H), 7.86 (m, 1H), 7.70 (s, 1H), 7.60 (d, 1H), 4.28 (br s, 2H), 4.09 (s, 3H), 3.17 (br s, 2H), 2.15 (br s, 4H) ppm. MS (ESI) 306 (M)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-49d1a36a294e437b8780efe6fcf84552
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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