5-Aminoindole → HCID 135891275, compound

HRID 712551Notes

Reaction equation

HRID 712551 reaction equation
N1C2C(=CC(N)=CC=2)C=C1.Br[C:12]1[N:17]=[C:16]2[N:18]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[CH:26]=[CH:25]4)[C:19](=[O:21])[NH:20][C:15]2=[N:14][CH:13]=1.C[O:33][C:34]1[CH:35]=[C:36](C2C=C3C(C4C=C5C(=CC=4)NC=C5)=CNC3=NC=2)[CH:37]=[CH:38][C:39]=1OC.OC1C=CC(B(O)O)=CC=1.COC1C=C(B(O)O)C=C(OC)C=1OC.BrC1N=C2N(C3C=C4C(=CC=3)NC=C4)C(=O)NC2=NC=1>>[OH:33][C:34]1[CH:35]=[CH:36][C:37]([C:12]2[N:17]=[C:16]3[N:18]([C:22]4[CH:23]=[C:24]5[C:28](=[CH:29][CH:30]=4)[N:27]([CH3:31])[CH:26]=[CH:25]5)[C:19](=[O:21])[NH:20][C:15]3=[N:14][CH:13]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 6

HCID 788675-AminoindoleHCID 27343604-Hydroxyphenylboronic acidHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 462340115-(3,4-dimethoxyphenyl)-3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridineHCID 727136326-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneHCID 86662679HCID 86662679, compound2×

Product 1

HCID 135891275HCID 135891275, compound

Procedure

Compound BE was prepared by a method analogous to that described in Example 1 by substituting 1-methyl-1H-indol-5-amine for 1H-indol-5-amine in the reaction with Intermediate BA to prepare 6-bromo-1-(1-methyl-1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. In a procedure similar to that used to synthesize Compound D, 4-hydroxyphenylboronic acid was substituted for 3,4,5-trimethoxyphenylboronic acid and 6-bromo-1-(1-methyl-1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one was substituted for 6-bromo-1-(1H-indol-5-yl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one to obtain the title compound. 2.2 mg recovered. HPLC retention time: 2.18 minutes. MS ESI (m/z): 358.2 (M+H)+, calc. 357.

Workup

  1. customCompound BE was prepared by a method analogous to
  2. customin the reaction with Intermediate BA

Sources & evidence

ORD record
ord-0f5fdc66126f4b508b152e4e2557bba2
Source dataset
uspto-grants-2015_11
Patent number
US09181247B2

Reaction notes

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