7-Methylindole → HCID 117902854, compound

HRID 1772162Notes

Reaction equation

HRID 1772162 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[CH:13]2.[F:17][C:18]1[CH:23]=[C:22](F)[CH:21]=[C:20]([F:25])[N:19]=1>CS(C)=O.C(Cl)Cl>[F:17][C:18]1[CH:23]=[C:22]([N:15]2[C:16]3[C:12](=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:7])[CH:13]=[CH:14]2)[CH:21]=[C:20]([F:25])[N:19]=1

Participants

6

Reactant 3

HCID 702757-MethylindoleHCID 27832892,4,6-TrifluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 117902854HCID 117902854, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium tert-butoxide (410 mg, 3.6 mmol) is added to a mixture of 7-methyl-1H-indole (470 mg, 3.6 mmol) in DMSO (20 ml) with ice cooling. Stirring is continued for 10 minutes before 2,4,6-trifluoropyridine E (350 μl, 3.6 mmol) is added dropwise. The mixture is warmed to RT and stirred for 2 h. The mixture is diluted with DCM and extracted with water. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 350 mg (40%). HPLC-MS: M+H=245; tR=1.03 min (Method—2).

Workup

  1. additionis added dropwise
  2. stirringstirred for 2 h
  3. extractionextracted with water
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-92baba949e6842bc9aaac6bda0a7eb5c
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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