Tetrabutylammonium Fluoride → HCID 68812543, compound

HRID 2105016Notes

Reaction equation

HRID 2105016 reaction equation
[Si]([O:8][C:9]1[C:10]([F:57])=[C:11]([N:17]([CH2:26][C:27]2[N:28]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:31]=2)[C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:15]([C:13]1[CH:14]=[C:9]([OH:8])[C:10]([F:57])=[C:11]([N:17]([CH2:26][C:27]2[N:28]([C:38]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:29]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:31]=2)[C:18]2[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=2)[CH:12]=1)[CH3:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68814522HCID 68814522, compound

Product 1

HCID 68812543HCID 68812543, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 191.1 (72 mg, 0.0936 mmol) in 1 mL THF at rt, was added TBAF (1 M in THF, 0.094 mL, 0.094 mmol). The mixture was stirred at rt for 30 min, then concentrated. The mixture was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes gradient) to afford 42 mg of Intermediate 191.2 as a colorless residue.

Workup

  1. concentrationconcentrated
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with H2O (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-95e28a25bd6846b1b002a4b2f5e707ea
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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