2-(Tributylstannyl)furan → 7-(acetylamino)-9a-butyl-8-chloro-6-fluoro4-(2-furyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372509Notes

Reaction equation

HRID 1372509 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)CCC.[C:19]([NH:22][C:23]1[C:35]([Cl:36])=[C:34]2[C:26]([C:27]3[C:32]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33]2)[CH2:31][CH2:30][C:29](=[O:41])[C:28]=3Br)=[CH:25][C:24]=1[F:43])(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([NH:22][C:23]1[C:35]([Cl:36])=[C:34]2[C:26]([C:27]3[C:32]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33]2)[CH2:31][CH2:30][C:29](=[O:41])[C:28]=3[C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)=[CH:25][C:24]=1[F:43])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 210720087-(acetylamino)-4-bromo-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 210720117-(acetylamino)-9a-butyl-8-chloro-6-fluoro4-(2-furyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 101.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Tributyl(2-furyl)stannane (0.47 mL, 1.7 mmol) was added to a mixture of 7-(acetylamino)-4-bromo-9a-butyl-8-chloro-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.367 g, 0.86 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.121 g, 0.17 mmol) in anhydrous toluene (8.6 mL). The mixture was purged with N2, then stirred and heated in an oil bath at 100° C. for 2 hours. After cooling to room temperature, the mixture was added to a pad of silica gel and the product eluted with EtOAc (20 mL). The solvent was evaporated and the residue (0.93 g) was purified by Biotage flash chromatography on a 40S silica gel column (4×7 cm) using 2:1 hexane-EtOAc as eluting solvent. The product containing fractions were concentrated under vacuum to provide crude 7-(acetylamino)-9a-butyl-8-chloro-6-fluoro4-(2-furyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.362 g) as an orange foam.

Workup

  1. customThe mixture was purged with N2
  2. temperatureAfter cooling to room temperature
  3. additionthe mixture was added to a pad of silica gel
  4. washthe product eluted with EtOAc (20 mL)
  5. customThe solvent was evaporated
  6. customthe residue (0.93 g) was purified by Biotage flash chromatography on a 40S silica gel column (4×7 cm)
  7. washas eluting solvent
  8. additionThe product containing fractions
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-f92f91c18983414fa11959a2f3054142
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

Loading…