MAGNESIUM SILICATE (synthetic) → 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

HRID 2072997Notes

Reaction equation

HRID 2072997 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[N:13]=[C:14]1[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 14390499HCID 14390499, compound

Product 1

HCID 143904722-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[3-[(4-bromobenzoyl)amino]-2-pyridinyl]glycine ethyl ester (4.6 g, 0.012 mole) was heated in glass in a 190° C. oil bath for 1/2 hour. The melt was cooled and methylene chloride (150 ml) added. The solution was twice treated with 25 g of Florisil® and filtered. The filtrate was concentrated in vacuo and the residue recrystallized from isopropyl ether-ethanol to give 2.1 g (49%) of a white flocculent solid, mp 138°-139° C.

Workup

  1. temperatureThe melt was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue recrystallized from isopropyl ether-ethanol
  5. customto give 2.1 g (49%) of a white flocculent solid, mp 138°-139° C.

Sources & evidence

ORD record
ord-7565e266fc1d41e38c8b9bb93d8aafbb
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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