Dichloromethane ethylacetate → HCID 136360208, compound

HRID 2099596Notes

Reaction equation

HRID 2099596 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[C:19]2[NH:23][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:21][C:20]=2[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(Cl)Cl.CCOC(C)=O>CO.O1CCCC1.[Pd]>[C:24]1([C:22]2[NH:23][C:19]([C:16]3[CH:15]=[CH:14][CH:13]=[C:12]4[C:17]=3[CH:18]=[C:9]([OH:8])[CH:10]=[CH:11]4)=[C:20]([C:30]3[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=3)[N:21]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 21226138Dichloromethane ethylacetateHCID 69054939HCID 69054939, compound

Product 1

HCID 136360208HCID 136360208, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-(7-benzyloxy-naphthalen-1-yl)-2-phenyl-1H-imidazol-4-yl]-pyridine (810 mg, 1.79 mmol) in methanol (50 mL) and tetrahydrofuran (10 mL) is added 10% Pd/C (100 mg) and the mixture is stirred for 3 hours under hydrogen atmosphere (1 atm). The catalyst is filtered and washed with ethyl acetate. The filtrate is concentrated and silica gel chromatography (CH2Cl2/EtOAc=1/1) afforded 8-(2-phenyl-5-pyridin-4-yl-3H-imidazol-4-yl)-naphthalen-2-ol (520 mg, 80% yield) as a syrup; 1H NMR 400 Hz (CD3OD) δ 6.89 (d, J=2.32 Hz, 1H), 7.17 (dd, J=2.38, 8.89 Hz, 1H), 7.48 (dd, J=7.15, 8.21 Hz, 1H), 7.55 (m, 3H), 7.66 (dd, J=1.09, 7.04 Hz, 1H), 7.91 (d, J=8.93 Hz, 1H), 7.95 (d, J=7.03 Hz, 3H), 8.04 (d, J=8.24 Hz, 1H), 8.10 (m, 2H), 8.47 (d, J=7.02 Hz, 2H); MS m/z (M+H+) 364.20.

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-8acbb24640364495a3ba3278577a8dc2
Source dataset
uspto-grants-2009_08
Patent number
US07569593B2

Reaction notes

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