Tetrabutylammonium Fluoride → 3-(1,3-Benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine

HRID 908438Notes

Reaction equation

HRID 908438 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[C:28]1[C:29]([NH2:40])=[N:30][CH:31]=[C:32]([C:34]#[C:35][Si](C)(C)C)[CH:33]=1>C1COCC1>[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[C:28]1[C:29]([NH2:40])=[N:30][CH:31]=[C:32]([C:34]#[CH:35])[CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 673889873-(1,3-Benzoxazol-2-yl)-5-(2-trimethylsilylethynyl)pyridin-2-amine

Product 1

HCID 866301533-(1,3-Benzoxazol-2-yl)-5-ethynyl-pyridin-2-amineYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride 1.0M in THF (0.629 ml) was added to a stirred solution of 3-(1,3-benzoxazol-2-yl)-5-(2-trimethylsilylethynyl)pyridin-2-amine (0.370 g) in THF (10 ml) at room temperature. The resulting solution was stirred for 1 hour. A yellow precipitate appeared during the reaction. After concentration, the crude product was purified by flash chromatography on silica gel eluting with 0 to 15% ethyl acetate in dichloromethane to afford 3-(1,3-benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine (225 mg) as a solid; NMR Spectrum: (DMSOd6) 4.20 (s, 1H), 7.42-7.51 (m, 2H), 7.80 (dd, 1H), 7.85 (dd, 1H), 8.04 (bs, 2H), 8.31 (d, 1H), 8.36 (d, 1H); Mass spectrum: M+H+: 236

Workup

  1. customA yellow precipitate appeared during the reaction
  2. concentrationAfter concentration
  3. customthe crude product was purified by flash chromatography on silica gel eluting with 0 to 15% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-5bc58a734f324fcda3fded0c2d0d0aa5
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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