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

HRID 1365480Notes

Reaction equation

HRID 1365480 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.C(O)(C(F)(F)F)=O.C(Cl)Cl>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

7

Reactant 5

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 469421185-Nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 92211H-IndazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the Rink resin (corresponding to fragment A9 of table I, 11 g, 0.85 mmol/g, 9.35 mmol) in anhydrous DMF (15 ml), 5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (2.9 g, 14.03 mmol), TBTU (4.5 g, 14.03 mmol) and DIPEA (3.62 g, 28.05 mmol) 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 (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 (12.5 g). 0.01 g of the resin were cleaved (1 ml of 40% TFA/DCM) to give an off-white solid (0.0014 mg, 82%).

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-34848b586af14af188f38b189712f92e
Source dataset
uspto-grants-2011_02
Patent number
US07888508B2

Reaction notes

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