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

HRID 1365481Notes

Reaction equation

HRID 1365481 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-4b4fbf224302491292d9d6f843524723
Source dataset
uspto-grants-2011_02
Patent number
US07888508B2

Reaction notes

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