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 992013Notes

Reaction equation

HRID 992013 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[NH:13][CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1>[Pd].C(O)C>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[NH:13][CH:12]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]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 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of of 3-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-5-fluoro-1H-indole (8.5 g) and 10% palladium on carbon (2.72 g) in ethanol (200 ml) was hydrogenated for 5 hours. The catalyst was filtered off and the solvent removed under vacuum. Chromatography (methanol-methylene chloride) afforded 7.55 g (82%) of product as a white solid: mp 183-185° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-0d7d385690da49f9964b51af26d8dc36
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

Loading…