Tetrafluoroborate → 2-(2-((Trimethylsilyl)ethynyl)phenyl)butanamide

HRID 592337Notes

Reaction equation

[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH2:18][CH3:19])[C:15]([NH2:17])=[O:16].F[B-](F)(F)F>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C>[CH3:4][Si:3]([C:1]#[C:2][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([CH2:18][CH3:19])[C:15]([NH2:17])=[O:16])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethynyltrimethylsilane (0.11 mL, 0.80 mmol) and dry DMF (9.0 mL) was added to a mixture of 2-(2-iodophenyl)butanamide (I2) (193 mg, 0.668 mmol), PdCl2(PPh3)2 (23 mg, 0.033 mmol), t-Bu3PH.BF4 (10 mg, 0.033 mmol) and CuI (6 mg, 0.033 mmol) under nitrogen. The resulting solution was degassed with a stream of nitrogen for 10 minutes before the addition of Et3N (3.0 mL). The resulting mixture was stirred at 60° C. under nitrogen for 16 hours then adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound I3 as a tan coloured solid (151 mg, 87); 1H NMR (400 MHz, d6-DMSO) δ 7.46-7.39 (m, 2H), 7.34 (td, J=7.7, 1.4 Hz, 1H), 7.26 (br, 1H), 7.21 (td, J=7.5, 1.4 Hz, 1H), 6.97 (br, 1H), 3.80 (dd, J=8.9, 5.7 Hz, 1H), 1.95-1.80 (m, 1H), 1.69-1.55 (m, 1H), 0.85 (t, J=7.3 Hz, 3H), 0.25 (s, 9H). LCMS-A: rt 6.267 min; m/z 260 [M+H]+.

Workup

customThe resulting solution was degassed with a stream of nitrogen for 10 minutes before the addition of Et3N (3.0 mL)
custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record: ord-c243bd82b6f6466a806e78e549f25276
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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