4,7-Dibromofuro[3,2-c]pyridine → 7-Bromofuro[3,2-c]pyridine

HRID 911945Notes

Reaction equation

HRID 911945 reaction equation
Br[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([Br:11])=[CH:4][N:3]=1.C(O[Na])=O>CN(C=O)C.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:11][C:5]1[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:2]=[N:3][CH:4]=1

Participants

7

Reactant 2

HCID 179854894,7-Dibromofuro[3,2-c]pyridineHCID 178526064HCID 178526064, compound

Product 1

HCID 179853197-Bromofuro[3,2-c]pyridineYield 77%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4,7-dibromofuro[3,2-c]pyridine (3.50 g, 12.6 mmol), HCO2Na (2.59 g, 38.1 mmol) and Pd(PPh3)4 (360 mg, 0.32 mmol) in dry DMF (35 mL) was heated at 100° C. (bath temperature) under Ar for 9 h. LC-MS showed the reaction was almost complete. The mixture was diluted with water (50 mL) and EtOAc (200 mL). Layers were separated and the organic phase was washed with water (3×40 mL), brine (40 mL), and dried over Na2SO4. The solvent was removed and residue was purified by silica gel chromatography eluting with Hexanes-EtOAc (80:20→70:30) to provide the title compound as an off-white solid (1.92 g, 77%). 1H NMR (CDCl3, 400 MHz): δ=6.98 (d, J=2.3 Hz, 1H), 7.79 (d, J=2.3 Hz, 1H), 8.62 (s, 1H), 8.89 (s, 1H).

Workup

  1. customLayers were separated
  2. washthe organic phase was washed with water (3×40 mL), brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customresidue was purified by silica gel chromatography
  6. washeluting with Hexanes-EtOAc (80:20→70:30)

Sources & evidence

ORD record
ord-c33fe607182f417193569678ab3bc69e
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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