Cesium carbonate → HCID 118159567, compound

HRID 628412Notes

Reaction equation

HRID 628412 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:12]([CH3:15])=[N:13][N:14]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[NH:8][C:6]=2[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1>CN(C=O)C.O>[Cl:1][C:2]1[C:3]2[N:4]([C:12]([CH3:15])=[N:13][N:14]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 136963104HCID 136963104, compound

Product 1

HCID 118159567HCID 118159567, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-chloro-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.150 g, 0.680 mmol, from Example 228, Step 6) and Cs2CO3 (0.88 g, 2.7 mmol) in DMF (2.10 mL) was added 2-(chloromethyl)pyridine hydrochloride (0.139 g, 0.850 mmol, Aldrich). The reaction was stirred overnight, then diluted with water and extracted with three portions of 5% iPrOH in DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% MeOH in DCM. Yield: (206 mg, 97%).

Workup

  1. extractionextracted with three portions of 5% iPrOH in DCM
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography
  6. washeluting with a gradient from 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-fe792b9e63c143979a65dfe1f58dd61b
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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