3-Fluoro-4-iodonitrobenzene → N-(2-Fluoro-4-nitrophenyl)-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

HRID 2240228Notes

Reaction equation

HRID 2240228 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1.[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1I.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[NH:11][C:9]1[C:10]2[C:2]([CH3:1])=[CH:3][N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[C:5]=2[N:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 2301023-Fluoro-4-iodonitrobenzeneHCID 23676156Sodium t-butoxideHCID 593050073-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Product 1

HCID 59304977N-(2-Fluoro-4-nitrophenyl)-3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 29 mg (100 μmol) of 3-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine, 33 mg (130 μmol) of 2-fluoro-1-iodo-4-nitrobenzene, 5 mg (10 μmol) of tris-(dibenzylideneacetone)dipalladium, 6 mg (10 mmol) of 1,1′-bis(diphenylphosphino)ferrocene and 14 mg (150 mmol) of sodium tert-butoxide in 3 ml of degassed toluene is stirred at 100° C. overnight. After cooling to RT, the reaction mixture is directly applied to a silica gel column and separated (mobile phase: cyclohexane/ethyl acetate 10:1 to 8:2).

Workup

  1. customseparated (mobile phase: cyclohexane/ethyl acetate 10:1 to 8:2)

Sources & evidence

ORD record
ord-59620fe7ac33493a8f744a96b6e5cafb
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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