1H-Pyrrolo(2,3-b)pyridine → 1H-Indazole

HRID 217959Notes

Reaction equation

HRID 217959 reaction equation
C(N1[C:9]2=[N:10][CH:11]=[C:12]([N+]([O-])=O)[CH:13]=[C:8]2[C:7]([C:17](O)=O)=C1)(C)(C)C.CC(C)[N:22]=C=NC(C)C.CCN(C(C)C)C(C)C.N1C2C(=CC=CN=2)C=C1>C(Cl)Cl.CN(C=O)C>[NH:22]1[C:7]2[C:8](=[CH:13][CH:12]=[CH:11][CH:17]=2)[CH:9]=[N:10]1

Participants

6

Reactant 4

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 12734DiisopropylcarbodiimideHCID 81531DiisopropylethylamineHCID 669243961H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid, 1-(1,1-dimethylethyl)-5-nitro-

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To the AMEBA II resin (0.1 g, 1 mmol/g, 0.1 mmol) in DCM/DMF (1:1, 2 ml), 1-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (3 eq), DIC (1.5 eq) DMAP (0.5 eq) and DIPEA (1 eq) were added. The reaction mixture was shaken at room temperature for 20 hours and then the resin was isolated by filtration. The resin was washed sequentially with DMF (2 ml), DCM (2 ml), DMF (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml) and dried in vacuo to give the resin bound 7-azaindole.

Workup

  1. customthe resin was isolated by filtration
  2. washThe resin was washed sequentially with DMF (2 ml), DCM (2 ml), DMF (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml), MeOH (2 ml), DCM (2 ml)
  3. customdried in vacuo
  4. customto give the resin

Sources & evidence

ORD record
ord-985801bdca9e4e6e9c6ea0c17f7e1139
Source dataset
uspto-grants-2012_06
Patent number
US08198298B2

Reaction notes

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