Acetic Acid → 7-(4-Bromo-2-chlorophenylamino)-8-chloro-3-methylaminomethylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

HRID 494726Notes

Reaction equation

HRID 494726 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:7]([Cl:16])[C:8]2[N:9]([C:11]([CH:14]=O)=[CH:12][N:13]=2)[CH:10]=1)=[O:4].C(O)(=O)C.[CH3:30][NH2:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:7]([Cl:16])[C:8]2[N:9]([C:11]([CH2:14][NH:31][CH3:30])=[CH:12][N:13]=2)[CH:10]=1)=[O:4]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 865967817-(4-Bromo-2-chlorophenylamino)-8-chloro-3-formyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 688627777-(4-Bromo-2-chlorophenylamino)-8-chloro-3-methylaminomethylimidazo[1,2-a]pyridine-6-carboxylic acid methyl esterYield 46.8%

Procedure

A suspension of 7-(4-bromo-2-chlorophenylamino)-8-chloro-3-formylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (58) (25 mg, 0.056 mmol), acetic acid (7 μL, 0.11 mmol), and methylamine (2.0 M solution in THF, 56 μL, 0.11 mmol) was stirred for 0.5 hours. Sodium triacetoxyborohydride (36 mg, 0.17 mmol) was added and the solution allowed to stir overnight. The reaction mixture was concentrated to dryness and purified by flash column chromatography (dichloromethane followed by 10:1 dichloromethane/methanol) to provide the desired product as a yellow solid (12 mg, 46%). MS (APCI+) m/z 455, 457, 459 (M+; Cl, Br pattern) detected.

Workup

  1. stirringto stir overnight
  2. concentrationThe reaction mixture was concentrated to dryness
  3. custompurified by flash column chromatography (dichloromethane followed by 10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-2c07ce9226e04c398775c29aae5f629a
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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