1-methyl-3-(1-methylindolin-6-yl)-4-nitro-1H-pyrrolo[2,3-b]pyridine → 1-methyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 331005Notes

Reaction equation

HRID 331005 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([N+:11]([O-])=O)=[C:5]2[C:4]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[CH3:23])=[CH:16][CH:15]=2)=[CH:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:5]=2[C:4]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[CH3:23])=[CH:16][CH:15]=2)=[CH:3]1

Participants

4

Reactant 1

HCID 710903071-methyl-3-(1-methylindolin-6-yl)-4-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 710901301-methyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-amineYield 43.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

To a stirred suspension of 1-methyl-3-(1-methylindolin-6-yl)-4-nitro-1H-pyrrolo[2,3-b]pyridine (D18) (3.1 g, 10.05 mmol) in ethanol (75 mL) was added 10% palladium on carbon (1.070 g, 1.005 mmol). The mixture was then stirred under hydrogen environment (4 bar) at RT for ca. 24 hours. Extra 10% palladium on carbon (1.070 g, 1.005 mmol) was added and the mixture was stirred under hydrogen (4 bar) at RT for another 24 hours. Additional 10% palladium on carbon (1.070 g, 1.005 mmol) was added and the mixture continued stirring under hydrogen atmosphere at RT for overnight (ca. 16 hours). The reaction mixture was filtered through celite. Washed celite with excess ethanol and the filtrate was concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-20% MeOH in DCM to give the title compound (1.21 g). LCMS (A): m/z (M+H)+ 279, C17H18N4 requires 278 (acidic).

Workup

  1. stirringthe mixture was stirred under hydrogen (4 bar) at RT for another 24 hours
  2. stirringthe mixture continued stirring under hydrogen atmosphere at RT for overnight (ca. 16 hours)
  3. filtrationThe reaction mixture was filtered through celite
  4. washWashed celite with excess ethanol
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a gradient of 0-20% MeOH in DCM

Sources & evidence

ORD record
ord-19e02b1e745e4ed4ac3fdafb35ece5da
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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