Triethylamine → 3-Fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline

HRID 2240219Notes

Reaction equation

HRID 2240219 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=2[F:29])[CH:3]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[F:29][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=1[CH2:19][C:4]1[CH:3]=[CH:2][N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])[CH:9]=[CH:10][C:5]=12)[NH2:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 593050056-Chloro-4-(2-fluoro-4-nitrobenzyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 593049903-Fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

270 mg (0.62 mmol) of 6-chloro-4-(2-fluoro-4-nitrobenzyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine are dissolved in 2 ml of ethanol. 170 μl (1.24 mmol) of triethylamine and 50 mg of 10% palladium-on-carbon are added. The mixture is hydrogenated at RT and a hydrogen pressure of 1.5 bar for 20 h. The mixture is filtered and concentrated, ethyl acetate is added and the mixture is washed with 1N aqueous sodium hydroxide solution. The organic phase is dried over sodium sulfate and concentrated. The product is reacted further without purification.

Workup

  1. customis hydrogenated at RT
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated
  4. additionethyl acetate is added
  5. washthe mixture is washed with 1N aqueous sodium hydroxide solution
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe product is reacted further without purification

Sources & evidence

ORD record
ord-9ba49cb5785e4ead9e01ca56ea373308
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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