Dimethylformamide → 2-(3-bromo-phenyl)-3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazine

HRID 38067Notes

Reaction equation

HRID 38067 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:10]([SH:13])[NH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:21][CH2:22][CH2:23]Br.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:10]3[S:13][CH2:21][CH2:22][CH2:23][N:11]3[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178527913HCID 178527913, compound

Product 1

HCID 674240152-(3-bromo-phenyl)-3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazineYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3-Bromo-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (60 mg, 0.22 mmol), 1,3-dibromopropane (22 ul, 0.22 mmol), K2CO3 (152 mg, 1.1 mmol) and dry DMF (5 ml) were reacted at room temperature for 16 hours. Water was added and the reaction extracted with ethyl acetate. The pooled organic extracts were washed with brine, dried over sodium sulphate and evaporated down. The crude material was purified by flash column chromatography eluting with ethyl acetate:hexane (1:1) to give a white solid (50% yield over two steps).

Workup

  1. extractionthe reaction extracted with ethyl acetate
  2. washThe pooled organic extracts were washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated down
  5. customThe crude material was purified by flash column chromatography
  6. washeluting with ethyl acetate:hexane (1:1)
  7. customto give a white solid (50% yield over two steps)

Sources & evidence

ORD record
ord-5108424330584365b9a042905f62173c
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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