Pyridine → HCID 21072007, compound

HRID 1372524Notes

Reaction equation

HRID 1372524 reaction equation
[NH2:1][C:2]1[C:14]([F:15])=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:20])[C:7]=3[Br:21])=[CH:4][C:3]=1[F:22].[C:23](Cl)([CH3:25])=[O:24].N1C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl.CCO>[C:23]([NH:1][C:2]1[C:14]([F:15])=[C:13]2[C:5]([C:6]3[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:20])[C:7]=3[Br:21])=[CH:4][C:3]=1[F:22])(=[O:24])[CH3:25]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 10270475HCID 10270475, compound

Product 1

HCID 21072007HCID 21072007, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-amino-4-bromo-9a-butyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one(0.131 g, 0.354 mmol) in CH2Cl2 (3 mL) was treated with AcCl (0.051 mL, 0.708 mmol) and pyridine (0.043 mL, 0.531 mmol). The resulting solution was stirred under a nitrogen atmosphere for 5 hours. This mixture was treated with NaOH (5N, 1 mL) and EtOH (6 mL), and stirred for 10 minutes. After being diluted with CH2Cl2, the mixture was dried over MgSO4, filtered through a pad of silica gel and rinsed with EtOAc. The filtrate was evaporated under vacuum. The crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing with 50% EtOAc in hexanes, to afford 7-(acetylamino)-4-bromo-9a-butyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.131 g, 90%) as yellow foam.

Workup

  1. stirringstirred for 10 minutes
  2. dry with materialthe mixture was dried over MgSO4
  3. filtrationfiltered through a pad of silica gel
  4. washrinsed with EtOAc
  5. customThe filtrate was evaporated under vacuum
  6. customThe crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate

Sources & evidence

ORD record
ord-a63105672cf34c04ae13139c0bb8ff3e
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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