Water → (1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrile

HRID 2169430Notes

Reaction equation

HRID 2169430 reaction equation
[N:1]1([C:10]2([CH2:15][C:16]([NH2:18])=O)[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.N1C(Cl)=NC(Cl)=NC=1Cl.C(OCC)(=O)C.O>CN(C)C=O.CCCCCC>[N:1]1([C:10]2([CH2:15][C:16]#[N:18])[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 867260602-(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)acetamide

Product 1

HCID 86726061(1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrileYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetamide (398) (1.6 g, 6.58 mmol) in dimethylformamide (25 mL) was added cyanuric chloride (728 mg, 3.95 mmol) at room temperature. The reaction mixture was stirred for 30 min at room temperature (TLC, 30% ethyl acetate in hexane, Rf=0.8). Cold water was added and the mixture was extracted with ethyl acetate (2×50 mL) and washed with water (2×50 mL) and brine (50 mL). The organic phase was thereafter dried and concentrated to get a crude product. The crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to get (1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-acetonitrile (399) (861 mg, 58%) as a light yellow thick oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. customThe organic phase was thereafter dried
  4. concentrationconcentrated
  5. customto get a crude product
  6. customThe crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6880419386004c759e5009f708717246
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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