Potassium Carbonate → HCID 67618089, compound

HRID 1029728Notes

Reaction equation

HRID 1029728 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][N:29]=[C:30]=[O:31]>C1COCC1>[CH3:28][NH:29][C:30](=[O:31])[O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([NH:11][CH2:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])[CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 67618170HCID 67618170, compound

Product 1

HCID 67618089HCID 67618089, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(3-fluoro-4-pyridinyl)propylamino]-1H-indol-5-ol (2.5 g) in 50 ml THF was added potassium carbonate (1.2 g), followed by methyl isocyanate (0.53 ml). After stirring at ambient temperature for three hours, the mixture was filtered, and the filtrate was concentrated to give a solid, 3.0 g, m.p. 165°-166° C. This material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined and concentrated to give a solid, 2.7 g, m.p. 177°-178° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a solid, 3.0 g, m.p. 165°-166° C
  4. washThis material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC
  5. concentrationconcentrated
  6. customto give a solid, 2.7 g, m.p. 177°-178° C.

Sources & evidence

ORD record
ord-f4fcab8af8dc4536806201481d43d4c3
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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