Dichloromethane → HCID 59333319, compound

HRID 1893451Notes

Reaction equation

HRID 1893451 reaction equation
Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:5]2=[N:4][CH:3]=1)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[CH:9][CH:8]=3.[C:24]([Si:26]([CH3:29])([CH3:28])[CH3:27])#[CH:25].C(Cl)Cl.[Cl-].[NH4+]>C(N(CC)CC)C.[Cu](I)I>[CH3:27][Si:26]([C:24]#[C:25][C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH2:17][CH2:18][OH:19])[C:5]2=[N:4][CH:3]=1)=[CH:11][C:10]([C:20]([F:23])([F:22])[F:21])=[CH:9][CH:8]=3)([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 25070093HCID 25070093, compound

Product 1

HCID 59333319HCID 59333319, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 3-{[1-bromo-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol as prepared in example 2 (100 mg, 0.26 mmol), ethynyltrimethylsilane (81 μL, 0.57 mmol) and copper iodide (5 mg, 0.026 mmol) in anhydrous triethylamine (3.5 mL) degassed under argon for 10 minutes was added Pd(dppf)Cl2.DCM (11 mg, 0.013 mmol). The mixture was stirred at 90° C. for 1 h45 and then allowed to cool to room temperature, poured onto a saturated aqueous solution of ammonium chloride and extracted three times with ethyl acetate/tetrahydrofuran (1:1). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1) to afford the title compound (80 mg, 75%) as an off-white solid.

Workup

  1. customdegassed under argon for 10 minutes
  2. additionwas added Pd(dppf)Cl2
  3. temperatureto cool to room temperature
  4. extractionextracted three times with ethyl acetate/tetrahydrofuran (1:1)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-6e972a78a9014e3d88e6843cc6e51de8
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…