Triphenylphosphine → HCID 59333330, compound

HRID 1893458Notes

Reaction equation

HRID 1893458 reaction equation
[C:1]([C:3]1[N:7]2[C:8]3[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:6]2=[N:5][CH:4]=1)=[CH:12][C:11]([C:27]([F:30])([F:29])[F:28])=[CH:10][CH:9]=3)#[CH:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:50]1([C:56](Cl)=[O:57])[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>C(N(CC)CC)C.[Cu](I)I>[N:50]1([C:56](=[O:57])[C:2]#[C:1][C:3]2[N:7]3[C:8]4[C:13]([N:14]=[C:15]([NH:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]5[CH2:26][CH2:25][CH2:24][CH2:23][O:22]5)[C:6]3=[N:5][CH:4]=2)=[CH:12][C:11]([C:27]([F:28])([F:29])[F:30])=[CH:10][CH:9]=4)[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 848104-Morpholinecarbonyl chlorideHCID 59333289HCID 59333289, compound

Product 1

HCID 59333330HCID 59333330, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-ethynyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]-7-(trifluoromethyl)imidazo [1,2-a]quinoxalin-4-amine (46 mg, 0.11 mmol), copper iodide (1 mg, 0.0055 mmol), triphenylphosphine (3 mg, 0.11 mmol) and Pd(PPh3)Cl2 (1.5 mg, 0.0022 mmol) in anhydrous triethylamine (0.5 mL) was added morpholine-4-carbonyl chloride (17 μL, 0.16 mmol) under an argon atmosphere. The mixture was stirred at 80° C. for 40 h, poured onto water and extracted four times with ethyl acetate. 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 (17 mg, 30%) as a yellow gum.

Workup

  1. additionpoured onto water
  2. extractionextracted four times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-c941597d311642fd99366d8a49408e5d
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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