Water → HCID 77231001, compound

HRID 2175109Notes

Reaction equation

HRID 2175109 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[NH:9]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:8][C:4]1[N:3]=[C:2]([N:9]2[CH2:15][CH2:14][CH2:13][CH:12]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 67247956HCID 67247956, compound

Product 1

HCID 77231001HCID 77231001, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

545 mg (2.3 mmol) of 2,6-dibromopyridine, the product from step c (428 mg, 2.3 mmol) and 954 mg of potassium carbonate (6.9 mmol) are suspended in 20 ml of DMSO and stirred at 120° C. overnight. Water is then added to the mixture, which is then extracted with EA. The organic phase is washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue formed is purified by means of RP flash chromatography on C18 silica gel.

Workup

  1. extractionis then extracted with EA
  2. washThe organic phase is washed with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue formed
  6. customis purified by means of RP flash chromatography on C18 silica gel

Sources & evidence

ORD record
ord-255b73a6a86846b4bd3754cd913ef620
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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