Trifluoroacetic acid → HCID 9946378, compound

HRID 1883612Notes

Reaction equation

HRID 1883612 reaction equation
Br[C:2]1[C:7]2[O:8][CH:9]3[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH:10]3[C:6]=2[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH:3]=1.FC(F)(F)[C:32](O)=[O:33]>CCOC(C)=O.C[O-].[Na+].CO.C(Cl)Cl.[Cu]Br>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[C:4]1[CH:3]=[C:2]([O:33][CH3:32])[C:7]2[O:8][CH:9]3[CH:10]([CH2:11][NH:12][CH2:13][CH2:14]3)[C:6]=2[CH:5]=1

Participants

8

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23508114HCID 23508114, compound

Product 1

HCID 9946378HCID 9946378, compound

Reagents, catalysts & solvents 5

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
85 °C

Procedure

In a 7 mL vial, copper (I) bromide (0.15 mmol, 22 mg) was diluted with 0.1 mL EtOAc and 0.6 mL of sodium methoxide in methanol (25 wt %). tert-Butyl 6-bromo-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.5 mmol, 250 mg) was added to the thick slurry and heated to 85° C. on the orbit shaker. An additional 0.1 mL of EtOAc was added. After 4.5 hr, the solvent was removed in vacuo. The resulting material was diluted with water and extracted three times with EtOAc. The combined organics were washed with brine, dried over NaSO4, decanted and concentrated to give crude yellow-brown oil. This material was diluted with 4 mL CH2Cl2 and cooled to 0° C. with an ice bath. After 15 min, 4 ml trifluoroacetic acid was added and the reaction was stirred at rt. After 2 hr the solvent was removed in vacuo to give crude oil after a NaOH workup. The crude material was purified by column chromatography (0.5/3.5/96 NH4OH/CH3OH/CH2Cl2) to give 105 mg colorless oil (60%).

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe resulting material was diluted with water
  3. extractionextracted three times with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over NaSO4
  6. customdecanted
  7. concentrationconcentrated
  8. customto give crude yellow-brown oil
  9. temperaturecooled to 0° C. with an ice bath
  10. waitAfter 15 min
  11. customAfter 2 hr the solvent was removed in vacuo

Sources & evidence

ORD record
ord-e0fbf7c4b3674653ad7d214de05f984f
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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