Tetrahydrofuran → HCID 58342010, compound

HRID 339600Notes

Reaction equation

HRID 339600 reaction equation
[Si]([SiH2][O:9][CH2:10][CH2:11][N:12]([CH3:37])[C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]4[CH:36]=3)=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl-].[NH4+]>CN(C=O)C>[OH:9][CH2:10][CH2:11][N:12]([CH3:37])[C:13]1[CH:14]=[CH:15][C:16](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]=[C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]4[CH:36]=3)=[CH:23][CH:22]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 131732066HCID 131732066, compound

Product 1

HCID 58342010HCID 58342010, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

To a stirred suspension of 4-[N-(2-tert-butyldimethylsilylsilanyloxyethyl)-N-methyl-4-{(E)-2-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]ethenyl}aniline (0.18 g, 0.362 mmol) in a mixture of dry THF (5 ml) and dry DMF (3 ml) at 0-5° C. was added a solution of TBAF in THF (1 M, 800 μl, 0.800 mmol). The reaction mixture was stirred at 0-5° C. for 5 min and then left to rise to room temperature and stirred for a further 50 min. A solution of saturated ammonium chloride (25 ml) was added to the reaction mixture and this was extracted with DCM/MeOH (1:1, 5×30 ml). The combined organics were washed with brine (40 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give a yellow oil that slowly solidified at room temperature. The solid was purified by flash chromatography (10:1 DCM/MeOH) to give the title compound (0.136 g, 98%) as a yellow solid.

Workup

  1. waitleft
  2. customto rise to room temperature
  3. stirringstirred for a further 50 min
  4. extractionthis was extracted with DCM/MeOH (1:1, 5×30 ml)
  5. washThe combined organics were washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure
  8. customto give a yellow oil that
  9. customslowly solidified at room temperature
  10. customThe solid was purified by flash chromatography (10:1 DCM/MeOH)

Sources & evidence

ORD record
ord-8724b55301494d08b9aea4758ea89731
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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