Dimethylformamide → HCID 86729997, compound

HRID 2199774Notes

Reaction equation

HRID 2199774 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[CH:8]=[C:7]([NH2:9])[N:6]=[N:5]1.Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1.CC([O-])(C)C.[K+].CN(C=O)C>O>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([NH:9][C:7]2[N:6]=[N:5][N:4]([CH2:3][O:2][CH3:1])[CH:8]=2)=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 23665647Potassium tert-butoxideHCID 86729996HCID 86729996, compound

Product 1

HCID 86729997HCID 86729997, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1-(methoxymethyl)-4-amino-1H-1,2,3-triazole (3.56 g, 27.784 mmol), 2,5-dibromopyridine (19.608 g, 82.773 mmol) and potassium tert-butylate (9.345 g, 83.252 mmol) were added into DMF (100 mL), heated to 70° C., and stirred for 72 hours. The reaction solution was poured into water, and extracted with ethyl acetate. The combined organic phase was washed with a saturated solution of sodium chloride, dried over anhydrous sodium sulfate, concentrated, and separated on a silica gel column chromatograph (ethyl acetate:petroleum ether=1:30) to obtain 0.318 g of 5-bromo-N-(1-(methoxymethyl)-1H-1,2,3-triazol-4-yl)pyridine-2-amine as a yellow solid, at a yield of 4%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phase was washed with a saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customseparated on a silica gel column chromatograph (ethyl acetate:petroleum ether=1:30)

Sources & evidence

ORD record
ord-f689e80a683d46e2a72ded2196c840ec
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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