Potassium Carbonate → HCID 86681000, compound

HRID 1847964Notes

Reaction equation

HRID 1847964 reaction equation
CS(O[CH2:6][C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12](Br)[S:13][C:9]=2[CH:8]=1)(=O)=O.[NH:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18]1.[C:26](=[O:29])([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N:17]1([CH2:6][C:7]2[CH:16]=[CH:15][C:10]3[N:11]=[C:12]([NH:11][C@@H:10]4[CH2:9][CH2:8][CH2:7][CH2:6][C@H:26]4[OH:29])[S:13][C:9]=3[CH:8]=2)[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67504Imidazo(4,5-b)pyridineHCID 86680990HCID 86680990, compound

Product 1

HCID 86681000HCID 86681000, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-bromobenzo[d]thiazol-6-yl)methyl methanesulfonate (900 mg, 2.79 mmol) from Step 3 of Example 2 and 1H-imidazo[4,5-b]pyridine (365 mg, 3.07 mmol) in DMF (8 mL) was added potassium carbonate (560 mg, 3.14 mmol) at rt. The reaction mixture was stirred at rt overnight. It was then diluted with 80 mL of EtOAc and the resulting mixture was washed with water and brine. The organic layer was separated and dried over MgSO4, and concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture of MeOH—CH2Cl2 (1:20, v/v) as eluent to give three isomers:

Workup

  1. washthe resulting mixture was washed with water and brine
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on a silica gel column
  6. additiona mixture of MeOH—CH2Cl2 (1:20, v/v) as eluent
  7. customto give three isomers

Sources & evidence

ORD record
ord-2141725463e8440abfb797e046ddc5c2
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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