Dimethylformamide → HCID 86670598, compound

HRID 401452Notes

Reaction equation

HRID 401452 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=2)[CH:7]=1.[CH3:13][O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18](B(O)O)=[CH:17][N:16]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>C(OCC)(=O)C>[CH3:13][O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH:11]=[O:12])=[CH:9][N:10]=3)[CH:7]=2)=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 213456766-Bromoimidazo[1,2-a]pyridine-3-carbaldehyde2×

Product 1

HCID 86670598HCID 86670598, compoundYield 47.43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde (Compound of step 1 of Intermediate 1, 200 mg, 0.89 mmol), 2,4-dimethoxypyrimidin-5-ylboronic acid (212.57 mg, 1.15 mmol), dichlorobis(triphenylphosphine) palladium (II) (20 mg, 10% mmol) and 2M aqueous Na2CO3 (1 mL) were added to DMF (8 mL) and refluxed for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with H2O and brine. The solvent was evaporated to obtain crude product, which was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 47.43%; 1H NMR (DMSO-d6; 300 MHz): δ 9.97 (s, 1H), 9.59 (s, 1H), 8.56-8.58 (d, 2H, J=4.5 Hz), 7.88-7.98 (m, 2H), 3.96 (s, 3H), 3.98 (s, 3H); MS: m/z 285.1 (M+1)+

Workup

  1. temperaturerefluxed for 3 hours
  2. washwashed with H2O and brine
  3. customThe solvent was evaporated
  4. customto obtain crude product, which
  5. customwas purified by column chromatography (silica gel, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-05b75b473ac24f3ab2d2175897225bb4
Source dataset
uspto-grants-2014_06
Patent number
US08741932B2

Reaction notes

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