Diisopropylamine → HCID 67417872, compound

HRID 625942Notes

Reaction equation

HRID 625942 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21].C(NC(C)C)(C)C>C1COCC1.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:8][N:6]1[CH:7]=[C:2]([C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH:3]=[C:4]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]1=[O:9]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 86675486HCID 86675486, compound

Product 1

HCID 67417872HCID 67417872, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}pyridin-2(1H)-one (2.92 g, 8.74 mmol) in 20 mL THF was added trimethylsilylacetylene (1.72 g, 17.47 mmol), copper (I) iodide (166 mg, 0.874 mmol), diisopropylamine (1.25 mL, 8.74 mmol), and PdCl2(dppf)-DCM adduct (713 mg, 0.874 mmol). This mixture was microwaved in a sealed vial at 145° C. for 10 minutes. After cooling, the mixture was filtered to remove solids, evaporated, and purified by flash chromatography (50 g silica gel, 0-40% ethyl acetate in hexane) to afford 1-methyl-3-{[2-(trimethylsilyl)ethoxy]methoxy}-5-[(trimethylsilyl)ethynyl]pyridin-2(1H)-one as a dark, viscous oil (2 g, 65% yield). LCMS [M+H]+=352.6

Workup

  1. customThis mixture was microwaved in a sealed vial at 145° C. for 10 minutes
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customto remove solids
  5. customevaporated
  6. custompurified by flash chromatography (50 g silica gel, 0-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8e4d451b76df46c1bf9eeb01c458cf00
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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