Butyl isocyanate → HCID 67619367, compound

HRID 1029739Notes

Reaction equation

HRID 1029739 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)[C:14]([CH3:22])=[CH:13]1.C([O-])([O-])=O.[K+].[K+].[CH2:29]([N:33]=[C:34]=[O:35])[CH2:30][CH2:31][CH3:32]>O1CCCC1>[CH2:29]([NH:33][C:34](=[O:35])[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]=[C:14]2[CH3:22])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 70146441HCID 70146441, compound

Product 1

HCID 67619367HCID 67619367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution consisting of 1-[(3-fluoro-4-pyridinyl)propylamino]-3-methyl-1H-indol-5-ol (2.10 g) and tetrahydrofuran (47 ml) was added milled K2CO3 (1.02 g) followed by dropwise addition of butyl isocyanate (0.87 ml) at room temperature under nitrogen. Stirring was continued for 15 hours, at which time the reaction mixture was filtered through a pad of celite and the solids washed with EtOAc. Concentration afforded the crude product. Purification via flash column chromatography (silica gel, ether) afforded 2.3 g of the desired product as an oil. The product was crystallized from ether/pentane, m.p. 83°-84° C.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. washthe solids washed with EtOAc
  4. concentrationConcentration
  5. customafforded the crude product
  6. customPurification via flash column chromatography (silica gel, ether)

Sources & evidence

ORD record
ord-c8875b540fcc4d1f8ca2281e9edb6839
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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