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

HRID 217957Notes

Reaction equation

HRID 217957 reaction equation
[N+]([C:4]1[CH:5]=[C:6]2[C:12]([C:13](O)=O)=C[NH:10][C:7]2=N[CH:9]=1)([O-])=O.C[N:17](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.N1C2C(=CC=CN=2)C=C1>CN(C=O)C>[NH:17]1[C:12]2[C:6](=[CH:5][CH:4]=[CH:9][CH:13]=2)[CH:7]=[N:10]1

Participants

6

Reactant 4

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 469421185-Nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the resin (1.5 g, 0.77 mmol/g, 1.16 mmol) of example 7 in anhydrous DMF (15 ml), it was added 5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (0.359 g, 1.73 mmol), TBTU (0.556 g, 1.73 mmol) and DIPEA (0.44 g, 3.48 mmol). 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 (25 ml), DCM (25 ml), DMF (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), TBME (25 ml×2) and dried in vacuo to give the resin bound 7-azaindole (1.70 g).

Workup

  1. customthe resin was isolated by filtration
  2. washThe resin was washed sequentially with DMF (25 ml), DCM (25 ml), DMF (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), DCM (25 ml), MeOH (25 ml), TBME (25 ml×2)
  3. customdried in vacuo
  4. customto give the resin

Sources & evidence

ORD record
ord-9cde50e08c924ed3af54c0b4fb454e61
Source dataset
uspto-grants-2012_06
Patent number
US08198298B2

Reaction notes

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