2,3-Diaminotoluene → HCID 178424027, compound

HRID 1982936Notes

Reaction equation

HRID 1982936 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]=O)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=1[NH2:21].[S]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[NH:20][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([CH3:13])[C:15]=4[N:21]=3)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 175932,3-DiaminotolueneHCID 5362487SulfurHCID 178520049HCID 178520049, compound

Product 1

HCID 178424027HCID 178424027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde Compound 5a (50 mg, 0.22 mmol) and 3-methyl-benzene-1,2-diamine Compound 5b (27 mg, 0.22 mmol) and sulfur (9 mg, 0.28 mmol) in DMF (1 mL) was heated to 100° C. overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-3-(4-methyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridine Compound 5c (50 mg, 69% yield) as a grey powder. 1H NMR (400 MHz, MeOD) δ 9.03 (s, 1H), 8.68 (s, 1H), 7.18 (t, 1H, J=8.4 Hz), 7.09 (m, 2H), 2.69 (s, 3H); MS (ESI) m/z: 329 (M+H+).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a88dc97f4daf4246ac780fad8ccedce2
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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