Triethylamine → HCID 86712692, compound
Reaction equation
[CH2:1]([Si:3]([C:8]#[CH:9])([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].CCN(CC)CC.Br[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[CH2:25][C:26]([O:28][CH3:29])=[O:27].F[B-](F)(F)F>CN(C=O)C.CCOC(C)=O.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>[CH3:24][C:22]1[CH:23]=[CH:18][C:19]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:20]([C:9]#[C:8][Si:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:21]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 70 °C
Procedure
A solution of triethylsilyl acetylene (0.27 mL, 1.5 mmol) in degassed DMF (4 mL) and Et3N (2.0 mL, 15 mmol) was added to a mixture of methyl 2-(2-bromo-4-methylphenyl)acetate (A84) (0.30 g, 1.2 mmol), PdCl2(PPh3)2 (0.043 g, 0.062 mmol), CuI (0.012 g, 0.062 mmol) and t-Bu3PH.BF4 (0.018 g, 0.062 mmol) in degassed DMF (10 mL). The resulting mixture was heated at 70° C. for 17 hours then diluted with EtOAc and passed through a plug of Celite, washing with EtOAc (150 mL). The filtrate was concentrated under reduced pressure and adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-15% EtOAc in petroleum spirits) to yield the title compound A85 as a yellow oil (0.326 g, 72% purity contaminated with starting material); 1H NMR (400 MHz, CDCl3) δ 7.32 (s, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.12-7.08 (m, 1H), 3.82 (s, 2H), 3.68 (s, 3H), 2.31 (s, 3H), 1.05 (t, J=7.9 Hz, 9H), 0.72-0.64 (m, 6H).
Workup
- washwashing with EtOAc (150 mL)
- concentrationThe filtrate was concentrated under reduced pressure
- custompurified by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-15% EtOAc in petroleum spirits)
Sources & evidence
- ORD record
- ord-01c0f3c0d15b4b82b4dc33386ccad1b3
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266864B2
Reaction notes
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