Tetrabutylammonium Fluoride → HCID 59852950, compound

HRID 1670336Notes

Reaction equation

HRID 1670336 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:4]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:7][CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59853054Carbamic acid, [6-[(trimethylsilyl)ethynyl]-3-pyridinyl]-, 1,1-dimethylethyl ester

Product 1

HCID 59852950HCID 59852950, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 6-(2-(trimethylsilyl)ethynyl)pyridin-3-ylcarbamate (62 mg, 0.21 mmol) in THF (5 mL) was cooled to −15° C. and treated with 1.0 M tetrabutylammonium fluoride (Aldrich, 0.25 mL, 0.25 mmol) and stirred for 40 min. The mixture was concentrated in vacuo and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (45 mg, 100%) as an off-white solid. 1H NMR (DMSO-d6) δ 9.78 (s, 1H), 8.58 (d, 1H, J=2.5 Hz), 7.92-7.84 (m, 1H), 7.46 (d, 1H, J=8.6 Hz), 4.17 (s, 1H), 1.47 (s, 9H); MS (ESI+): m/z 219.20 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. washThe EtOAc phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5299794fb30c4b848f6fd9dbc2b55510
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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