Trifluoroacetic acid → HCID 118021326, compound

HRID 2284524Notes

Reaction equation

HRID 2284524 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][NH:22]2.C([SiH](CC)CC)C>ClCCl.O>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][C:20]2[C:19]3[C:23](=[CH:24][CH:25]=[CH:26][C:18]=3[CH3:17])[NH:22][CH:21]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052Triethylsilane2×HCID 707414-BromobenzaldehydeHCID 852824-Methylindole

Product 1

HCID 118021326HCID 118021326, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add TFA (114.4 mmol) to a solution of 4-bromobenzaldehyde (76.2 mmol), 4-methylindole (76.2 mmol), and triethylsilane (228.4 mmol) in dichloromethane (10 mL) pre-cooled in an ice bath. Allow the mixture to warm to room temperature and stir for 2 hours. Add additional triethylsilane (228.4 mmol) and warm the mixture to 30° C. overnight in an oil bath. Dilute the reaction with water (100 mL) and extract with dichloromethane (2×100 mL). Separate and wash the organic phase with water (2×100 mL) and brine (100 mL). Dry the organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography over silica gel (120 g cartridge) eluting with 0-10% ethyl acetate in petroleum ether to yield the title compound (8 g, 26.6 mmol): MS (m/z): 301 (M+1)

Workup

  1. temperaturepre-cooled in an ice bath
  2. temperaturewarm the mixture to 30° C. overnight in an oil bath
  3. additionDilute
  4. extractionextract with dichloromethane (2×100 mL)
  5. customSeparate
  6. washwash the organic phase with water (2×100 mL) and brine (100 mL)
  7. dry with materialDry the organic phase over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure
  10. customPurify the residue by flash chromatography over silica gel (120 g cartridge)
  11. washeluting with 0-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-5efb27612a4d48259b4b25d1072c7dbd
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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