1H-Indole, 5-(phenylmethoxy)-1-(4-pyridinylmethyl)- → HCID 15292694, compound

HRID 249283Notes

Reaction equation

HRID 249283 reaction equation
C1(C[O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:13]=[CH:12]3)C=CC=CC=1.[H][H]>C(O)C.[Pd]>[N:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:14]2[C:15]3[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 99049331H-Indole, 5-(phenylmethoxy)-1-(4-pyridinylmethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 15292694HCID 15292694, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 10% Pd/C (1.5 g) in 50 ml ethanol in a 500 ml Parr hydrogenation bottle, was added a suspension of 5-phenylmethoxy-1-(4-pyridinylmethyl)-1H-indole in 200 ml ethanol. The mixture was shaken at 50° C. under 50 psi hydrogen for one hour, then cooled, filtered, and the filtrate evaporated to a solid, 10 g, dec. 178° C. A sample of this material was eluted on a silica gel column with 2% methanol/dichloromethane via HPLC. The desired fractions were combined and evaporated to yield 2.3 g of 1-(4-pyridinylmethyl)-1H-indol-5-ol, as a solid, m.p. 185°-186° C.

Workup

  1. additionwas added
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to a solid, 10 g, dec
  5. custom178° C
  6. washA sample of this material was eluted on a silica gel column with 2% methanol/dichloromethane via HPLC
  7. customevaporated

Sources & evidence

ORD record
ord-707089cba0b74e749188e78d81a62162
Source dataset
uspto-grants-1993_05
Patent number
US05214058

Reaction notes

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