Potassium Carbonate → HCID 59627921, compound

HRID 2421226Notes

Reaction equation

HRID 2421226 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:4][CH:3]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu](I)I>[F:27][C:22]1[CH:21]=[C:20]([N:4]2[C:5]3[C:10](=[C:9]([O:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[CH:3]2)[CH:25]=[CH:24][C:23]=1[OH:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 23383468HCID 23383468, compound

Product 1

HCID 59627921HCID 59627921, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of 3-methyl-4-[(phenylmethyl)oxy]-1H-indole (R. A. Heacock et al. Canadian Journal of Chemistry, (1964), 42(3), 514) (617 mg, 2.60 mmol) in N-methyl-2-pyrrolidinone (10 mL) was added 4-bromo-2-fluorophenol (0.28 mL, 2.60 mmol), copper iodide (96 mg, 0.50 mmol) and potassium carbonate (867 mg, 6.28 mmol). The reaction mixture was heated in a Biotage Initiator™ Microwave Synthesizer at 190° C. for 3 hours. The mixture was filtered through a pad of Celite which was subsequently washed with ethyl acetate. The ethyl acetate solution was washed with water and then the aqueous layer re-extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and then concentrated in vacuo. The product was purified by silica gel chromatography eluting with 0-30% ethyl acetate in hexane to yield the title compound (D2) (147 mg).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite which
  2. washwas subsequently washed with ethyl acetate
  3. washThe ethyl acetate solution was washed with water
  4. extractionthe aqueous layer re-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by silica gel chromatography
  9. washeluting with 0-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2024c362292843c1b13d475a116d62f3
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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