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Acetic Acid → 2-(4-Chloro-2-methoxypyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69367
Notes
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Reaction equation

HRID 69367 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH:15]([CH3:17])[CH3:16])[C:5]2=[O:18].CC(O)=O.[Cl:23][C:24]1[C:29]([CH:30]=O)=[C:28]([O:32][CH3:33])[N:27]=[CH:26][CH:25]=1>CO>[Cl:23][C:24]1[CH:25]=[CH:26][N:27]=[C:28]([O:32][CH3:33])[C:29]=1[C:30]1[NH:11][C:10]2=[CH:9][C:8]3[C:7](=[O:14])[N:6]([CH:15]([CH3:17])[CH3:16])[C:5](=[O:18])[C:4]=3[CH:3]=[C:2]2[N:1]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 534079284-Chloro-2-methoxypyridine-3-carbaldehydeHCID 666902745-Amino-2-isopropyl-6-nitroisoindoline-1,3-dione

Product 1

HCID 666894972-(4-Chloro-2-methoxypyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dioneYield 41.8%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent
2×

Conditions

Temperature
-50 °C

Procedure

To a suspension of 5-amino-2-isopropyl-6-nitroisoindoline-1,3-dione (0.37 g) in 250 mL of MeOH was added 5 mL of AcOH. The resulting solution was degassed with argon and then charged with 10% Pd/C (0.12 g, 50% wet) and hydrogenated at 40 psi of hydrogen for 16 h. Another 2 mL of AcOH was added to the mixture and then solids were filtered off. The filtrate was cooled to −50° C. and a solution of 4-chloro-2-methoxynicotinaldehyde (0.31 g, 1.78 mmol) in 200 mL of MeOH was added dropwise under inert atmosphere. The resulting solution was allowed to warm up to rt and stirred for 16 h. Solvent was evaporated and the oily residue was purified by column chromatography (7.5% MeOH in dichloromethane) to give title compound as a solid (0.23 g, 29.3%). 1H NMR (500 MHz, CDCl3) δ 8.18 (s, 1H), 8.12 (d, 1H), 8.03 (s, 1H), 7.90 (d, 1H), 6.92 (d, 1H), 6.75 (d, 1H), 5.39 (s, 2H), 4.56 (p, 1H), 3.72 (s, 3H), 3.61 (s, 3H), 1.50 (d, 6H). ESI MS: m/z 371.1 (M+1).

Workup

  1. customThe resulting solution was degassed with argon
  2. additioncharged with 10% Pd/C (0.12 g, 50% wet) and hydrogenated at 40 psi of hydrogen for 16 h
  3. additionAnother 2 mL of AcOH was added to the mixture
  4. filtrationsolids were filtered off
  5. temperatureto warm up to rt
  6. customSolvent was evaporated
  7. customthe oily residue was purified by column chromatography (7.5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-00d29ae654a14edaa15a6957c62fdc02
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822500B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes