HCID 59146119, compound → HCID 59146036, compound

HRID 1512857Notes

Reaction equation

HRID 1512857 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5]2.[Cu][C:20]#[N:21]>CN(C=O)C.[Cu]I>[C:20]([C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5]2)#[N:21]

Participants

5

Reactant 2

HCID 59146119HCID 59146119, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59146036HCID 59146036, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl 3-(5-bromo-7-fluoro-1H-indol-2-yl)propanoate (D161) (650 mg), copper(I) iodide (394 mg) in DMF (5 mL) was added copper(I) cyanide (741 mg). The reaction vessel was sealed and heated in Biotage Initiator using initial very high to 200° C. for an hour. After cooling the reaction, the precipitate was filtered, and the filtrate was diluted with EtOAc (30 mL). The organic phase was washed with brine (25 mL), water (25 mL×2). The organic layer was dried over sodium sulphate and the crude product was purified by column chromatography to give ethyl 3-(5-cyano-7-fluoro-1H-indol-2-yl)propanoate (D162) (400 mg) as a yellow solid. MS (ES): C14H13FN2O2 requires 260; found 261.1 (M+H+).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in Biotage Initiator
  3. waitusing initial very high to 200° C. for an hour
  4. temperatureAfter cooling
  5. customthe reaction
  6. filtrationthe precipitate was filtered
  7. additionthe filtrate was diluted with EtOAc (30 mL)
  8. washThe organic phase was washed with brine (25 mL), water (25 mL×2)
  9. dry with materialThe organic layer was dried over sodium sulphate
  10. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ad0f3e39703f401daaacf490a806ba47
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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