Methane → 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

HRID 621880Notes

Reaction equation

HRID 621880 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][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].C>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][CH:18]=[C:17]([Cl:21])[CH:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 14390494N-[3-[(3-chlorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester

Product 1

HCID 156171872-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid N-[3-[(3-chlorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester, 12.84 g (0.038 mole) was heated in glass at 210°-20° C. in a Wood's metal bath for 7 minutes. The residue was dissolved in methylene chloride, treated with charcoal, and filtered through a Celite pad. The orange filtrate was treated with Florisil® to give a pink filtrate. The filtrate was evaporated to give a solid, which was recrystallized from tetrahydrofuran-petroleum ether. The solid was collected, washed with petroleum ether, and dried under high vacuum at 50° C. for 5 hours to give 5.3 g (44%) of title compound, mp 98°-99.8° C.

Workup

  1. filtrationfiltered through a Celite pad
  2. additionThe orange filtrate was treated with Florisil®
  3. customto give a pink filtrate
  4. customThe filtrate was evaporated
  5. customto give a solid, which
  6. customwas recrystallized from tetrahydrofuran-petroleum ether
  7. customThe solid was collected
  8. washwashed with petroleum ether
  9. customdried under high vacuum at 50° C. for 5 hours

Sources & evidence

ORD record
ord-50cb1345929143f7aa59da66741cd953
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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