HCID 59627919, compound → HCID 44193186, compound

HRID 2421252Notes

Reaction equation

HRID 2421252 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:16]3[C:11](=[C:12]([O:17]CC4C=CC=CC=4)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:25])[CH:5]=[CH:4][C:3]=1[OH:26]>C(O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=3[CH:10]=[C:9]2[CH3:25])[CH:5]=[CH:4][C:3]=1[OH:26]

Participants

6

Reactant 1

HCID 59627919HCID 59627919, compound

Product 1

HCID 44193186HCID 44193186, compoundYield 50.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-fluoro-4-{2-methyl-4-[(phenylmethyl)oxy]-1H-indol-1-yl}phenol (D3) (85 mg, 0.24 mmol) in ethanol (7 mL) was added a solution of tetra-n-butylammonium chloride (170 mg, 0.61 mmol) in ethyl acetate (1 mL). The solution was hydrogenated in an H-cube over a 10% Pd/C catalyst. The resulting solution was concentrated and the product purified by MDAP to yield the title compound (E3) (31 mg).

Workup

  1. concentrationThe resulting solution was concentrated
  2. customthe product purified by MDAP

Sources & evidence

ORD record
ord-0c1e4e773e9141dbbe3cd15ac926280e
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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