3-Fluoro-4-iodonitrobenzene → HCID 59304976, compound

HRID 2240235Notes

Reaction equation

HRID 2240235 reaction equation
[CH3:1][N:2]1[C:6]2[N:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:5]=2[CH:4]=[CH:3]1.[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=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:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[NH:11][C:10]1[C:5]2[CH:4]=[CH:3][N:2]([CH3:1])[C:6]=2[N:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 2301023-Fluoro-4-iodonitrobenzeneHCID 23676156Sodium t-butoxideHCID 552894121-Methyl-1H-pyrrolo[2,3-b]pyridin-4-amine

Product 1

HCID 59304976HCID 59304976, compound

Reagents, catalysts & solvents 3

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

Procedure

A solution of 260 mg (1.77 mmol) of 1-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine, 566 mg (2.12 mmol) of 2-fluoro-1-iodo-4-nitrobenzene, 81 mg (0.09 mmol) of tris(dibenzylidene-acetone)dipalladium, 98 mg (0.18 mmol) of 1,1′-bis(diphenylphosphino)ferrocene and 238 mg (2.47 mmol) of sodium tert-butoxide in 8 ml of degassed toluene is stirred at 100° C. overnight. After cooling to RT, the reaction mixture is applied directly to a silica gel column and separated (mobile phase: cyclohexane/ethyl acetate 10:1 to 1:1).

Workup

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

Sources & evidence

ORD record
ord-4728b22f56474e1383cd886728732d52
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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