HCID 58238625, compound → HCID 136177199, compound

HRID 1037655Notes

Reaction equation

HRID 1037655 reaction equation
FC1C=CC(C[O:7][C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH2:21])[N:15]=3)=[CH:12][CH:11]=[CH:10][C:9]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=CC=1>C(O)C.[Pd]>[C:22]1([CH:20]([C:16]2[N:15]=[C:14]([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:8]=3[OH:7])[CH:19]=[CH:18][CH:17]=2)[CH3:21])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 58238625HCID 58238625, compound

Product 1

HCID 136177199HCID 136177199, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound 10 (1.5 g, 3.3 mmol, 1.0 equiv) was dissolved in ethanol (50 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 18 hr. The reaction was filtered through a bed of Celite and rinsed with dichloromethane (100 mL). The product was absorbed onto silica gel (4 g) by concentration under reduced pressure. This material was purified on a silica gel column (30 g) by eluting with heptanes (200 mL), ethyl acetate (2%) in heptanes (200 mL), ethyl acetate (3%) in heptanes (200 mL) and ethyl acetate (4%) in heptanes (100 mL). The desired product was isolated pure in 87% yield (1.0 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 (4 g) by concentration under reduced pressure
  4. customThis material was purified on a silica gel column (30 g)
  5. washby eluting with heptanes (200 mL), ethyl acetate (2%) in heptanes (200 mL), ethyl acetate (3%) in heptanes (200 mL)

Sources & evidence

ORD record
ord-64ac59d004ff4f379ef411bff3d099d3
Source dataset
uspto-grants-2013_10
Patent number
US08546501B2

Reaction notes

Loading…