1H-Indazole → 5-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 250583Notes

Reaction equation

HRID 250583 reaction equation
B(O)O.Br[C:5]1[CH:6]=[C:7]2[C:11](=[N:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.CC1(C)C(C)(C)OB([C:22]2[CH:23]=[C:24]3C=CN[C:25]3=[N:26][CH:27]=2)O1.N1C2C(=CC=CC=2)C=N1>>[N:26]1[CH:27]=[CH:22][CH:23]=[C:24]([C:5]2[CH:6]=[C:7]3[CH:8]=[CH:9][NH:10][C:11]3=[N:12][CH:13]=2)[CH:25]=1

Participants

5

Reactant 4

HCID 92211H-Indazole2×HCID 61668Boronic AcidHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Procedure

Additional compounds were prepared following the protocol of Scheme 32, either by substituting pyridine-3-boronic acid with an appropriate boronic acid or by substituting the 5-bromo-7-azaindole with 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine and reacting with a suitable aryl or heteroaryl halide (i.e. coupling with the boronic acid ester on the azaindole, and the halide on the group to be coupled to the 5-position of the azaindole). The following compounds were prepared by this procedure:

Workup

  1. customAdditional compounds were prepared
  2. customThe following compounds were prepared by this procedure

Sources & evidence

ORD record
ord-d25de20224de4148b65b1e49bb297509
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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