Potassium Carbonate → HCID 15292696, compound

HRID 257797Notes

Reaction equation

HRID 257797 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:24]1([CH2:30][N:31]=[C:32]=[O:33])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:24]1([CH2:30][NH:31][C:32](=[O:33])[O:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH:9]=[CH:10]3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76639Benzyl isocyanateHCID 15292694HCID 15292694, compound

Product 1

HCID 15292696HCID 15292696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-pyridinylmethyl)-1H-indol-5-ol (2.2 g) in 50 ml tetrahydrofuran, was added milled K2CO3 (1.4 g) followed by phenylmethyl isocyanate (1.2 ml). After stirring at ambient temperature for twenty hours, the mixture was filtered, and the filtrate evaporated to an oil, (~3.5 g) which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined and evaporated to yield 2.8 g of 1-(4-pyridinylmethyl)-1H-indol-5-yl phenylmethylcarbamate, m.p. 112°-114° C.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated to an oil, (~3.5 g) which
  3. washwas eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC
  4. customevaporated

Sources & evidence

ORD record
ord-760d617a817d4ac8ba5a24c80e2b3b82
Source dataset
uspto-grants-1993_11
Patent number
US05264442

Reaction notes

Loading…