HCID 58238620, compound → HCID 136177201, compound

HRID 1037651Notes

Reaction equation

HRID 1037651 reaction equation
[CH:1]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[C:21]([O:32]CC3C=CC(F)=CC=3)=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:24][CH:25]=2)[N:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH:1]([C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:21]=2[OH:32])[CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58238620HCID 58238620, compound

Product 1

HCID 136177201HCID 136177201, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 6 (1.1 g, 2.1 mmol, 1.0 equiv) was dissolved in ethanol (60 mL) and 10% palladium (50% aqueous) on carbon (0.3 g) was added. The material was shaken on a Parr hydrogenator under a hydrogen atmosphere (30 psi) for 24 hr. The reaction was filtered through a layer of Celite and rinsed with dichloromethane (100 mL). The product was absorbed onto silica gel (3 g) by concentration under reduced pressure. This material was purified on a silica gel column (20 g) by eluting with ethyl acetate (2%) in heptanes (600 mL). The desired product was isolated pure in 45% yield (0.39 g).

Workup

  1. filtrationThe reaction was filtered through a layer of Celite
  2. washrinsed with dichloromethane (100 mL)
  3. customThe product was absorbed onto silica gel (3 g) by concentration under reduced pressure
  4. customThis material was purified on a silica gel column (20 g)
  5. washby eluting with ethyl acetate (2%) in heptanes (600 mL)

Sources & evidence

ORD record
ord-9df44f6ae92a463791e87f12d4ad5d9a
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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