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

HRID 2240211Notes

Reaction equation

[CH3:1][Si:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][CH:14]=[C:15]([NH2:16])[C:10]=2[CH:9]=[CH:8]1.[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1I.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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]>[F:19][C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[NH:16][C:15]1[C:10]2[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:18])([CH3:17])[CH3:1])[C:11]=2[N:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

50 mg (0.19 mmol) of 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-4-amine, 61 mg (0.23 mmol) of 2-fluoro-1-iodo-4-nitrobenzene and 26 mg (0.27 mmol) of sodium tert-butoxide are initially charged in 1 ml of toluene. The mixture is degassed. 8.7 mg (0.01 mmol) of tris(dibenzylideneacetone)dipalladium and 9.1 mg (0.02 mmol of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine are then added. The mixture is heated in a sealed vessel at 120° C. overnight. The mixture is then filtered through an Extrelut cartridge (mobile phase: dichloromethane/methanol 10:1) and purified by preparative HPLC.

Workup

customThe mixture is degassed
filtrationThe mixture is then filtered through an Extrelut cartridge (mobile phase: dichloromethane/methanol 10:1)
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-6390e00558394e6eaa67cbf0a811f55b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723347B2

Reaction notes

Loading…