Cesium fluoride → HCID 59425075, compound

HRID 502266Notes

Reaction equation

HRID 502266 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1.[Cl:19][C:20]1[S:21][C:22]2[CH:28]=[C:27](I)[CH:26]=[CH:25][C:23]=2[N:24]=1.[F-].[Cs+]>C(COC)OC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:19][C:20]1[S:21][C:22]2[CH:28]=[C:27]([C:8]3[N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:10]4[C:6]([CH:7]=3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=4)[CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 24728896tert-Butyl 6-methoxy-1H-indole-1-carboxylateHCID 594264122-Chloro-6-iodo-1,3-benzothiazole

Product 1

HCID 59425075HCID 59425075, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

tert-butyl 6-methoxy-1H-indole-1-carboxylate, from example 1BO, (2.50 g, 8.6 mmol) is dissolved in anhydrous dimethoxyethane (21.5 mL). To the solution is added 2-chloro-6-iodobenzothiazole (2.42 g, 8.2 mmol), cesium fluoride (2.53 g, 16.7 mmol) and PdCl2(PPh3)2 (0.23 g, 0.33 mmol). The reaction mixture is heated at reflux. After 17 h the reaction mixture is cooled to room temperature, diluted with water (100 mL) and extracted with ethyl acetate (4×20 mL). The extract is washed with saturated aqueous NaHCO3 (20 mL), dried over MgSO4 and concentrated under vacuum to give tert-butyl 2-(2-chlorobenzothiazol-6-yl)-6-methoxy-indole-1-carboxylate (2.95 g, 83%) as a hard foam.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate (4×20 mL)
  4. washThe extract is washed with saturated aqueous NaHCO3 (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b08221d48a2e490ebc756ea4cb6c0629
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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