Hydrochloric Acid → HCID 19759241, compound

HRID 248396Notes

Reaction equation

HRID 248396 reaction equation
Br[C:2]1[N:6]([CH2:7][CH3:8])[C:5]([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[C:18]4=[N:19][CH:20]=[CH:21][C:22]([CH3:23])=[C:17]4[N:16]=[C:15]3[CH2:24][CH2:25][CH3:26])=[CH:11][CH:10]=2)=[C:4]([C:29]#[N:30])[CH:3]=1.[OH-].[K+].Cl.C(N(CC)CC)C>CO.[Pd]>[C:29]([C:4]1[CH:3]=[CH:2][N:6]([CH2:7][CH3:8])[C:5]=1[C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:24][CH2:25][CH3:26])=[CH:11][CH:10]=1)#[N:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 19759526HCID 19759526, compound

Product 1

HCID 19759241HCID 19759241, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[4-(5-bromo-3-cyano-1-ethyl-2-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine and 3-[4-(4-bromo-3-cyano-1-ethyl-2-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imiazo[4,5-b]pyridine was dissolved in methanol (15 ml) and hydrogenated with 10% palladium on charcoal (300 mg) and potassium hydroxide (180 mg) at atmospheric pressure at ambient temperature for two hours. Concentrated hydrochloric acid was added until the pH of the solution was adjusted to 1 and then triethylamine was added until the pH was alkaline. The mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate to give 3-[4-(3-cyano-1-ethyl-2-pyrrolyl)benzyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed on silica gel
  4. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-8f1d38e4f4a94dec979ba129d7355f2c
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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