Methoxymethyl-triphenylphosphonium chloride → HCID 58574510, compound

HRID 1619354Notes

Reaction equation

HRID 1619354 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]CCCC.[F:29][C:30]1[CH:31]=[C:32]([C:36]#[C:37][C:38]2[CH:47]=[C:46]3[C:41]([C:42](=[O:54])[N:43]4[CH2:52][CH2:51][C:50](=O)[CH2:49][CH2:48][C:44]4=[N:45]3)=[CH:40][CH:39]=2)[CH:33]=[CH:34][CH:35]=1>C1COCC1>[F:29][C:30]1[CH:31]=[C:32]([C:36]#[C:37][C:38]2[CH:47]=[C:46]3[C:41]([C:42](=[O:54])[N:43]4[CH2:52][CH2:51]/[C:50](=[CH:2]\[O:3][CH3:4])/[CH2:49][CH2:48][C:44]4=[N:45]3)=[CH:40][CH:39]=2)[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 58574177HCID 58574177, compoundHCID 178418339Butyllithium

Product 1

HCID 58574510HCID 58574510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (methoxymethyl)triphenylphosphonium chloride (171 mg, 0.5 mmol, 1 equiv) in 5 mL THF at −78° C. was added n-BuLi (0.2 mL, 0.5 mmol, 1 equiv) dropwise and stirred at the same temperature for half an hour. A solution of 3-((3-fluorophenyl)ethynyl)-6,7,9,10-tetrahydroazepino[2,1-b]quinazoline-8,12-dione (173 mg, 0.5 mmol, 1 equiv) in THF was then added to the mixture dropwise at the same temperature and stirred for 2 hours. Then the reaction mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the desired product, which was purified by silica gel chromatography. MS (ESI): 375 (MH+).

Workup

  1. stirringstirred for 2 hours
  2. customThen the reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57dc2b1d20f944858cba3fda3e925fac
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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