Sodium Carbonate → N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide

HRID 1777523Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][CH2:12][CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:10].[Cl:26][C:27]1[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30](I)[C:28]=1[NH2:29].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:34][C:32]1[CH:31]=[C:30]2[C:28](=[C:27]([Cl:26])[CH:33]=1)[NH:29][C:15]([Si:16]([CH3:17])([CH3:18])[CH3:19])=[C:14]2[CH2:13][CH2:12][NH:11][C:9](=[O:10])[C:8]1[CH:20]=[CH:21][CH:22]=[C:6]([CH2:5][C:4]2[CH:23]=[CH:24][CH:25]=[C:2]([F:1])[CH:3]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide (0.130 g; 0.365 mmol), 2,4-dichloro-6-iodoaniline (0.127 g; 0.441 mmol), palladium (II) acetate (0.016 g; 0.073 mmol) and sodium carbonate (0.195 g; 1.84 mmol) in DMF (8 mL) was heated at 100° C. for 18 hours in a sealed tube and concentrated under reduced pressure. The residue was suspended in brine and extracted with dichloromethane (2×100 mL). The organic layer was dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to furnish 0.045 g (23%) of N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide.

Workup

concentrationconcentrated under reduced pressure
extractionextracted with dichloromethane (2×100 mL)
customThe organic layer was dried
concentrationconcentrated under reduced pressure
customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-a925906016124cd1a53d0272bf851e80
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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