HCID 58238618, compound → HCID 136177200, compound

HRID 1037656Notes

Reaction equation

HRID 1037656 reaction equation
[CH:1]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:21]=2[O:30]CC2C=CC=CC=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]([CH3:28])([CH3:27])[CH3:29])[C:21]=2[OH:30])[CH:17]=[CH:18][CH:19]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 58238618HCID 58238618, compound

Product 1

HCID 136177200HCID 136177200, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 12 (0.8 g, 1.66 mmol, 1.0 equiv) was dissolved in ethanol (30 mL) and 10% palladium (50% aqueous) on carbon (0.2 g) was added. The material was shaken on a Parr hydrogenator under a hydrogen atmosphere (30 psi) for 4 hr. The reaction was filtered through a bed 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 heptanes (250 mL) and ethyl acetate (1%) in heptanes (500 mL). The desired product was isolated pure in 77% yield (0.5 g).

Workup

  1. filtrationThe reaction was filtered through a bed 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 heptanes (250 mL) and ethyl acetate (1%) in heptanes (500 mL)

Sources & evidence

ORD record
ord-a33350e516ba4b8e88c244177cd5ea0c
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

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