Indole → HCID 15335320, compound

HRID 1449624Notes

Reaction equation

HRID 1449624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5]2.ClS([N:20]=[C:21]=O)(=O)=O.N1C2C(=CC=CC=2)C=C1.CN(C)C=O>C(#N)C.C(OCC)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([F:13])([F:15])[F:14])=[C:5]2[C:21]#[N:20]

Participants

8

Reactant 4

HCID 798IndoleHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 15335319HCID 15335319, compound

Product 1

HCID 15335320HCID 15335320, compoundYield 49.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloro-1-methyl-2-(trifluoromethyl)indole (1.79 g, 7.7 mmole) in acetonitrile is cooled to 0° C., treated with chlorosulfonylisocyanate (CSI) (1.0 mL 11.5 mmole) stirred until starting indole cannot be observed by thin layer chromatography, treated with 5 mL of dimethylformamide (DMF), stirred for 0.5 hour and diluted with diethyl ether and water. The phases are separated. The organic phase is washed with water, dried over Na2SO4 and concentrated in vacuo. The resultant residue is chromatographed using silica gel and 4:1 hexanes:ethyl acetate as eluent to give the title product as a white solid, 0.99 g (49.7% yield) mp 166°-167.5° C., identified by IR, 1HNMR, 13CNMR, 19FNMR and mass spectral analyses.

Workup

  1. stirringstirred for 0.5 hour
  2. customThe phases are separated
  3. washThe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue is chromatographed

Sources & evidence

ORD record
ord-83e719d4d8fb46499effcd13b54c4bd4
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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