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Formic Acid → HCID 15383547, compound

HRID 744979
Notes
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Reaction equation

HRID 744979 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[C:22]([NH:23][C:24]([CH:26]3[CH2:28][CH2:27]3)=O)=[C:21]([CH3:29])[C:20](Br)=[CH:19][N:18]=2)=[CH:11][CH:10]=1)#[N:2].C(O)=O.C(N(CC)CC)C>[Pd].C1(C)C=CC=CC=1>[CH:26]1([C:24]2[N:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])=[CH:10][CH:11]=3)[C:17]3=[N:18][CH:19]=[CH:20][C:21]([CH3:29])=[C:22]3[N:23]=2)[CH2:28][CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 15837815HCID 15837815, compound

Product 1

HCID 15383547HCID 15383547, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140Toluene
Solvent

Procedure

Toluene (30 ml) was added to 2.0 g (4.3 mmol) of 2-(2'-cyanobiphenyl-4-yl)methylamino-3-cyclopropanecarboxamido-5-bromo-4-methyl-pyridine, 1.0 g (21.7 mmol) of formic acid, 8.5 g (84.6 mmol) of triethylamine and 10% Pd-C (300 mg), followed by heating under reflux for 6 hours. After the reaction liquid was brought to room temperature and filtered to remove the catalyst, vacuum concentration was effected. Chloroform (100 ml) and water (50 ml) were added to the residue and the obtained mixture was caused liquid-liquid separation. The aqueous phase was further extracted with chloroform (50 ml) twice. The organic phases were combined, dried over anhydrous magnesium sulfate and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to give 1.3 g of 2-cyclopropyl-3-(2'-cyanobiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine (yield 82%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. customAfter the reaction liquid
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto remove
  7. concentrationthe catalyst, vacuum concentration
  8. additionChloroform (100 ml) and water (50 ml) were added to the residue
  9. customliquid-liquid separation
  10. extractionThe aqueous phase was further extracted with chloroform (50 ml) twice
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationsubjected to vacuum concentration
  13. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a2042cc6c8874ee5ae81d97b74696822
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05559236

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes