Methanol → HCID 59983191, compound

HRID 1643880Notes

Reaction equation

HRID 1643880 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12]([NH2:18])=[C:11]3[C:19]([F:22])([F:21])[F:20])=[CH:4][CH:3]=1.CO.N#N>CCOC(C)=O.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH:12]([NH2:18])[CH:11]3[C:19]([F:22])([F:20])[F:21])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887Methanol2×HCID 947NitrogenHCID 59983189HCID 59983189, compound

Product 1

HCID 59983191HCID 59983191, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 147B (400 mg, 1.3 mmol) in EtOAc (5 mL)-MeOH (15 mL) was bubbled with N2 for 15 min, then palladium hydroxide (20 weight % palladium on carbon) (200 mg) was added. The resulting suspension was subjected to hydrogenation under 80 psi of pressure for 16 h., then filtered. The filtrate was concentrated. The residue was chromatographed (silica gel) eluting with 20% EtOAc in hexane (100 mL), 50% EtOAc in hexane (100 mL), 100% ETOAc (100 mL), 5% MeOH in EtOAc (150 mL) to give title compound (62 mg, 15% yield) as a white foam.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customThe residue was chromatographed (silica gel)
  4. washeluting with 20% EtOAc in hexane (100 mL), 50% EtOAc in hexane (100 mL)

Sources & evidence

ORD record
ord-c53ec105867143e6bfd9a33226187eba
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

Loading…