Potassium Carbonate → HCID 9817189, compound

HRID 2294207Notes

Reaction equation

HRID 2294207 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+].[CH3:24][N:25]=[C:26]=[O:27]>O1CCCC1>[CH3:24][NH:25][C:26](=[O:27])[O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[CH:9]=[CH:10]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 15292694HCID 15292694, compound

Product 1

HCID 9817189HCID 9817189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-pyridinylmethyl)-1H-indol-5-ol (2.4 g) in 50 ml tetrahydrofuran, was added milled K2CO3 (1.5 g), followed by methyl isocyanate (0.65 ml). After stirring at ambient temperature for three hours, the mixture was filtered and the filtrate evaporated to a solid, 3.0 g, m.p. 170° C. This material was eluted on a silica gel column with 2% methanol/dichloromethane via high pressure liquid chromatography (HPLC) and the desired fractions were combined, then evaporated to yield 2.4 g of 1-(4-pyridinylmethyl)-1H-indol-5-yl methylcarbamate, as a solid, m.p. 179°-180° C.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated to a solid, 3.0 g, m.p. 170° C
  3. washThis material was eluted on a silica gel column with 2% methanol/dichloromethane via high pressure liquid chromatography (HPLC)
  4. customevaporated

Sources & evidence

ORD record
ord-8159b4e5d72c43d296a3818a4fc923a3
Source dataset
uspto-grants-1997_11
Patent number
US05688816

Reaction notes

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