Diisopropylethylamine → 6-bromo-N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-2-oxo-2H-chromene-3-carboxamide

HRID 240020Notes

Reaction equation

HRID 240020 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][C:16](=[O:21])[C:15]([C:22]([OH:24])=O)=[CH:14]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:49]1[C:50]([C:58]2[CH:59]=[C:60]([NH2:64])[CH:61]=[CH:62][CH:63]=2)=[CH:51][N:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=12>CN(C=O)C>[N:49]1[C:50]([C:58]2[CH:59]=[C:60]([NH:64][C:22]([C:15]3[C:16](=[O:21])[O:17][C:18]4[C:13]([CH:14]=3)=[CH:12][C:11]([Br:10])=[CH:20][CH:19]=4)=[O:24])[CH:61]=[CH:62][CH:63]=2)=[CH:51][N:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6944636-bromo-2-oxo-2H-chromene-3-carboxylic acidHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11782996-bromo-N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-2-oxo-2H-chromene-3-carboxamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (35.6 μL, 0.2 mmol) was added to 6-bromo-3-carboxy-coumarin (50.0 mg, 0.19 mmol) and HATU (77.7 mg, 0.2 mmol) in 2 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (38.9 mg, 0.19 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 61.4 mg of product in 68% yield: LCMS (ESI) m/z 461 (MH+).

Workup

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

Sources & evidence

ORD record
ord-fd652d02a6e9465b830573fbb1b5f273
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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