Potassium Carbonate → 2-(1-Benzofuran-2-yl)-6-methoxyimidazo[1,2-a]pyridine

HRID 501051Notes

Reaction equation

HRID 501051 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.Br[C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][N:17]2[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:14]1[N:15]=[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][N:17]2[CH:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 467379672-Bromo-6-methoxyimidazo[1,2-a]pyridine

Product 1

HCID 250149292-(1-Benzofuran-2-yl)-6-methoxyimidazo[1,2-a]pyridineYield 0.7%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzofuran boronic acid (0.289 mmol), 2-bromo-6-methoxyimidazo[1,2-a]pyridine (0.263 mmol), Pd(dppf)Cl2 (0.013 mmol) and K2CO3 (aq.) were stirred in DMF at 80° C. under argon for 1 h. The reaction mixture was allowed to cool to r.t. and brine was added. The reaction mixture was extracted with CH2Cl2 and the organic phase was filtered. The solvents were removed under reduced pressure and the residue purified by reverse phase HPLC to afford the title compound (0.5 mg). 1H NMR δ ppm 7.95 (s, 1 H) 7.67 (d, 1 H) 7.65-7.60 (m, 1 H) 7.58-7.51 (m, 2 H) 7.33-7.20 (m, 3 H) 7.03 (dd, 1 H) 3.86 (s, 3 H); MS m/z 265 (M+H).

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2
  2. filtrationthe organic phase was filtered
  3. customThe solvents were removed under reduced pressure
  4. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b254d3c57852407f8ca1e33f576e4d06
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

Loading…