Potassium Carbonate → HCID 70979520, compound

HRID 1485394Notes

Reaction equation

HRID 1485394 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][CH2:10][CH2:11][C:5]2=[N:4][N:3]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20](F)=[N:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([N:9]2[CH2:10][CH2:11][C:5]3=[N:4][N:3]=[C:2]([CH3:1])[N:6]3[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]2=3)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3458175-Chloro-2-fluoropyridineHCID 120995541-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

Product 1

HCID 70979520HCID 70979520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (300 mg, 1.5 mmol), 5-chloro-2-fluoropyridine (600 mg, 4.5 mmol) and K2CO3 (621 mg, 4.5 mmol) in 10 mL of DMF was stirred at 170° C. for 30 min. After the solvent was removed in vacuo, the product was purified by flash chromatography eluting with DCM:MeOH=10:1 to give 6-(5-chloropyridin-2-yl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine as a yellow solid. (50 mg, 11.3%).

Workup

  1. customAfter the solvent was removed in vacuo
  2. customthe product was purified by flash chromatography
  3. washeluting with DCM

Sources & evidence

ORD record
ord-50c7ab7295244a05b1bd8e932a8878bf
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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