Triethylamine → HCID 131734710, compound

HRID 1773471Notes

Reaction equation

HRID 1773471 reaction equation
I[C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[C:15]([C:27]([F:30])([F:29])[F:28])[CH:14]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].CCN(CC)CC.[CH3:38][Si:39]([C:42]#[CH:43])([CH3:41])[CH3:40]>[Cu]I.CN(C=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)=[C:15]([C:27]([F:30])([F:28])[F:29])[CH:14]=2)=[O:11])=[CH:3][C:2]=1[C:43]#[C:42][Si:39]([CH3:41])([CH3:40])[CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 118107769HCID 118107769, compound

Product 1

HCID 131734710HCID 131734710, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

The product (1.06 g, 2.0 mmol) obtained from Step 1, CuI (0.19 g, 0.1 mmol), Pd(PPh3)Cl2 (0.35 g, 0.5 mmol) and DMF (10 ml) were added into a 100 ml three-necked flask, and Et3N (0.52 g, 4.0 mmol) and trimethylsilylacetylene (0.98 g, 10 mmol) were added under the protection of an inert gas atmosphere. The mixture was reacted at 80° C. for 16 hours with stirring, and the system was cooled to room temperature, filtered, and extracted with ethyl acetate (50 ml×3) and H2O (50 ml). The organic phases were back-extracted with saturated brine, and the organic phases were combined, dried over anhydrous Na2SO4, and purified by column chromatography, to give a milky white solid.

Workup

  1. customThe mixture was reacted at 80° C. for 16 hours
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate (50 ml×3) and H2O (50 ml)
  4. extractionThe organic phases were back-extracted with saturated brine
  5. dry with materialdried over anhydrous Na2SO4
  6. custompurified by column chromatography
  7. customto give a milky white solid

Sources & evidence

ORD record
ord-c0c85903299a42f58597dc0ffc39907a
Source dataset
uspto-grants-2016_02
Patent number
US09255107B2

Reaction notes

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