Potassium Iodide → HCID 68650236, compound

HRID 1949109Notes

Reaction equation

HRID 1949109 reaction equation
[C:1]([N:8]1[C:20]2[C:19]([O:21][CH2:22][CH2:23]Br)=[C:18]3[N:25]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][C:31]=4[C:17]3=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([F:40])[CH:13]=2)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].OCC[N:44]1[CH2:50][CH2:49][CH2:48][N:47](C(OC(C)(C)C)=O)[CH2:46][CH2:45]1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+]>CS(C)=O.CC#N.CN(C=O)C>[N:44]1([CH2:23][CH2:22][O:21][C:19]2[C:20]3[N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C:9]4[C:14](=[CH:13][C:12]([F:40])=[CH:11][CH:10]=4)[C:15]=3[CH:16]=[C:17]3[C:31]4[CH:30]=[C:29]([F:32])[CH:28]=[CH:27][C:26]=4[N:25]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[C:18]=23)[CH2:50][CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 27356721-Boc-4-(2-hydroxyethyl)hoMopiperazine, 95%HCID 68650332HCID 68650332, compound

Product 1

HCID 68650236HCID 68650236, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,7-diBOC-2,10-difluoro-6-(2-bromoethoxy)indolo[2,3-b]carbazole (150.0 mg, 0.24 mmol), tert-butyl 4-(2-hydroxyethyl)-1,4-diazepane-1-carboxylate (97.6 mg, 0.49 mmol), a base (K2CO3 or Cs2CO3; 2-10 equiv) and potassium iodide (0.1 equivalent) in a anhydrous solvent (DMF, MeCN or DMSO; 30 mL per mmol) was heated to 80-90° C. for 1-2 hours. The reaction was cooled to room temperature and filtered. The solution was concentrated and dried under vacuum pump. The residue was purified by flash chromatography to provide the 6-(2-(1,4-diazepan-1-yl)ethoxy)-2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazole.

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated
  3. customdried under vacuum pump
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d463b312a2304814add86a65e27d58e2
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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