HCID 11842687, compound → HCID 57588502, compound

HRID 1782102Notes

Reaction equation

HRID 1782102 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:15][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pd]>[C:5]1([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:15][C:11]=3[N:10]=[CH:9]2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 11842687HCID 11842687, compound

Product 1

HCID 57588502HCID 57588502, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (EXAMPLE 1) (50 mg) and 10% Pd—C (100 mg) in ethanol (10 mL) and ethyl acetate (10 mL), was hydrogenated at atmospheric pressure for 16 h. The catalyst was removed by filtration through Celite and the filtrate concentrated in vacuo to yield ethyl 1-phenyl-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate EXAMPLE 2. LC-MS (ES+): m/z 256 [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ=1.46 (t, J=7.1 Hz, 3H), 4.42 (q, J=7.1 Hz, 2H), 7.22 (d, J=1.0 Hz, 1H), 7.48 (m, 1H), 7.69 (m, 2H), 7.94 (m, 2H), 8.73 (s, 1H), 12.28 (br s, 1H, NH).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4cc9605e04d242ada0ec88c62eaef81a
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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