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Triethylamine → ethyl 8-(2-Ethyl-6-methylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-carboxylate

HRID 1166169
Notes
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Reaction equation

HRID 1166169 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH:21]=O)[CH3:18].C([BH3-])#N.[Na+].C(N(CC)CC)C>CO.[Cl-].[Zn+2].[Cl-]>[CH2:17]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:20]=1[CH2:21][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:16])=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 22672637Ethyl 8-amino-3-methylimidazo[1,2-a]pyridine-2-carboxylateHCID 229974692-Ethyl-6-methylbenzaldehyde

Product 1

HCID 22997468ethyl 8-(2-Ethyl-6-methylbenzylamino)-3-methylimidazo[1,2-a]pyridin-2-carboxylateYield 8.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred mixture of ethyl 8-amino-3-methylimidazo[1,2-a]pyridin-2-carboxylate (1.53 g, 7.0 mmol) in methanol (25 ml) were added 2-ethyl-6-methylbenzaldehyde (1.1 g, 7.1 mmol), zinc(II)chloride (1.1 g, 8.0 mmol) in methanol (10 ml) and sodium cyanoborohydride (0.5 g, 8.0 mmol). The reaction mixture was refluxed for 4 h. and then stirred at room temperature for 20 h. Triethylamine (2.5 ml) was added and the mixture was stirred for 30 min. and evaporated under reduced pressure. Purification of the residue by column chromatography twice on silica gel using 1) methylene chloride:methanol (95:5) 2) heptane:isopropyl ether (1:5) as eluent gave 0.2 g (8%) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h.
  2. stirringthe mixture was stirred for 30 min.
  3. customevaporated under reduced pressure
  4. customPurification of the residue by column chromatography twice on silica gel using 1) methylene chloride:methanol (95:5) 2) heptane:isopropyl ether (1:5) as eluent

Sources & evidence

ORD record
ord-80da9f086b924dc391ffbf26a527ba0c
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06613775B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes