Diazomethane → 2-Diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone

HRID 2169427Notes

Reaction equation

HRID 2169427 reaction equation
[N:1]1([C:10]2([C:15](Cl)=[O:16])[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.[N+:18](=[CH2:20])=[N-:19].CNC(N)=O.[OH-].[K+]>O1CCCC1.CCOCC.CCCCCC.C(OCC)(=O)C>[N+:18](=[CH:20][C:15]([C:10]1([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:16])=[N-:19]

Participants

9

Reactant 4

HCID 9550DiazomethaneHCID 11719MethylureaHCID 14797Potassium HydroxideHCID 867260561-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride

Product 1

HCID 867260572-Diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanoneYield 90%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonyl chloride (395) (1.2 g, 8.83 mmol) in tetrahydrofuran (80 mL) was dropwise added a solution of diazomethane [which was freshly synthesized following the standard procedure, starting from methylurea via formation of NMU and followed by KOH treatment] in ether (80 mL) at −5° C., while stirring very slowly. The reaction mixture was left standing for 1 h at 0° C. (TLC, 30% ethyl acetate in hexane, Rf=0.6). Volatiles were removed to get the crude product which was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 2-diazo-1-(1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentyl)-ethanone (396) (1.1 g, 90%) as a yellow sticky solid.

Workup

  1. customwas freshly synthesized
  2. customat −5° C.
  3. waitThe reaction mixture was left
  4. customVolatiles were removed
  5. customto get the crude product which
  6. customwas purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f9ea4ec691ef41a98bd509573eefdf4d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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