Aniline → HCID 68780972, compound

HRID 2363713Notes

Reaction equation

HRID 2363713 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[I:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[C:21]([C:23](OCC)=[O:24])[N:22]=2)[C:18]=1[CH3:19].[Cl-].[NH4+]>C1(C)C=CC=CC=1>[I:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[C:21]([C:23]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:24])[N:22]=2)[C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 68780924HCID 68780924, compound

Product 1

HCID 68780972HCID 68780972, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 852 μL of aniline in 104 mL of toluene cooled to 0° C. are added dropwise 6.2 mL of a 2M solution of trimethylaluminium in toluene, followed by addition, at 20° C., of 1.5 g of ethyl 6-iodo-5-methyl(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylate. The reaction mixture is stirred for 2 hours at 20° C. The resulting mixture is cooled to 4° C. and 120 mL of saturated ammonium chloride solution are then added. After concentrating under reduced pressure, the residue is taken up in ethyl acetate and the organic phase is washed with water, dried over magnesium sulfate, filtered through Celite and evaporated to dryness under reduced pressure. The residue is triturated in methanol, filtered off and dried to give 1.15 g of 6-iodo-5-methyl-N-phenyl(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a yellow solid.

Workup

  1. temperatureThe resulting mixture is cooled to 4° C.
  2. concentrationAfter concentrating under reduced pressure
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is triturated in methanol
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-a5400051c23748b5a72bdb7ae737cf3a
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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