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Sodium Iodide → 8-(2-Fluoro-4-iodo-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester

HRID 2067018
Notes
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Reaction equation

HRID 2067018 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=1[F:22])=[O:4].[I-:23].[Na+].CN[C@@H]1CCCC[C@H]1NC.C(OCC)(=O)C>O1CCOCC1.CO.ClCCl.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:23])=[CH:17][C:16]=1[F:22])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 595651888-(4-Bromo-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester

Product 1

HCID 595652128-(2-Fluoro-4-iodo-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl esterYield 68.1%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 8-(4-bromo-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (235 mg, 0.65 mmol), copper (I) iodide (6 mg, 0.03 mmol), sodium iodide (195 mg, 1.3 mmol) and trans-N,N′-dimethyl-1,2-cyclohexane diamine (0.01 mL, 0.06 mmol) in 1,4-dioxane (1.0 mL) was heated at 110° C. for 26 hours under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with methanol and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2M NH3 in MeOH. The eluent was collected and concentrated to give a residue. The residue was subjected to flash chromatography (Si-PPC, gradient 0% to 20%, ethyl acetate in dichloromethane) to afford the title compound as a pale yellow solid (182 mg, 67%). LCMS (method B): RT=3.45 min, [M+H]+=412.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe cartridge was then washed with methanol
  3. washthe desired product was subsequently eluted
  4. customThe eluent was collected
  5. concentrationconcentrated
  6. customto give a residue

Sources & evidence

ORD record
ord-e994eb7e2135414989f9b2c1ef54d141
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293763B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes