Cesium carbonate → HCID 70981490, compound

HRID 1529161Notes

Reaction equation

HRID 1529161 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C=O)C.O>[CH:20]1([CH2:19][N:8]2[C:5]3=[N:6][CH:7]=[C:2]([F:1])[CH:3]=[C:4]3[C:10]([I:11])=[N:9]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2762531(Iodomethyl)cyclopentaneHCID 178505979HCID 178505979, compound

Product 1

HCID 70981490HCID 70981490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10.000 g (38.021 mmol) of 5-fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine and 13.627 g (41.823 mmol) of cesium carbonate were initially charged in 270 ml of DMF, and 8.785 g (41.823 mmol) of (iodomethyl)cyclopentane were added. The reaction mixture was stirred at RT overnight, diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. This gave 6.370 g of the target compound (purity 83%, 49% of theory), which was reacted further as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated on a rotary evaporator
  4. customThis gave 6.370 g of the target compound (purity 83%, 49% of theory), which was reacted further as a crude product

Sources & evidence

ORD record
ord-780f104b0bb64b3387de937b2c1a50d4
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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