3-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-fluoro-1H-indole → 3-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-fluoro-1H-indole

HRID 1275537Notes

Reaction equation

HRID 1275537 reaction equation
[CH2:1]1[O:20][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=4)[NH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3][CH2:2]1>[Pd].C(O)C>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=4)[NH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:20][CH2:1]1

Participants

4

Reactant 1

HCID 105163803-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-fluoro-1H-indole

Product 1

HCID 105643253-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-fluoro-1H-indoleYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(5-fluoro-1H-3-indolyl)-cyclohex-3-en-one ethylene ketal (2.7 g, 0.01 mol) and 10% palladium on carbon (1.2 g) in ethanol (200 ml) was hydrogenated for 4 days. The catalyst was filtered off and the filtrate was concentrated. The product was dried under vacuum to afford 2.8 g (100%) of product as a white solid: mp 183-185° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-efdcdd267f3b4f2cade45b0c69726392
Source dataset
uspto-grants-2000_12
Patent number
US06162803

Reaction notes

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