Potassium Hydroxide → Furo[3,2-c]pyridin-7-ol

HRID 911946Notes

Reaction equation

HRID 911946 reaction equation
Br[C:2]1[C:3]2[O:10][CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[OH-:11].[K+].C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>O.O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:10]1[C:3]2[C:2]([OH:11])=[CH:7][N:6]=[CH:5][C:4]=2[CH:8]=[CH:9]1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 11953610Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneHCID 179853197-Bromofuro[3,2-c]pyridine

Product 1

HCID 53486798Furo[3,2-c]pyridin-7-olYield 99.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-bromofuro[3,2-c]pyridine (9.15 g, 46.2 mmol), potassium hydroxide (7.78 g, 139 mmol), Pd2(dba)3 (0.02 eq) and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (0.08 eq) in H2O (22.5 mL) and 1,4-dioxane (22.5 mL) was vigorously stirred at 100° C. overnight. LC-MS showed completion of the reaction. The reaction mixture was washed with DCM (3×30 mL). The aqueous layer was neutralized and concentrated by freeze dryer. The resulting solid was washed with massive amount of acetone to give the title compound as a white solid (6.2 g, 81% yield). 1H NMR (DMSO-d6, 400 MHz): δ=7.05 (d, J=2.0 Hz, 1H), 8.04 (s, 1H), 8.06 (d, J=2.2 Hz, 1H), 8.44 (s, 1H). MS (ES+): m/z=136.15 [MH+].

Workup

  1. customcompletion of the reaction
  2. washThe reaction mixture was washed with DCM (3×30 mL)
  3. concentrationconcentrated by freeze dryer
  4. washThe resulting solid was washed with massive amount of acetone

Sources & evidence

ORD record
ord-442ad4a76e8b4e959e84ac92c83acbb2
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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