Triethylamine → HCID 66793261, compound

HRID 2069560Notes

Reaction equation

HRID 2069560 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[C:17][CH2:18][CH2:19]O)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.C(N(CC)CC)C.[B-](F)(F)(F)[F:29].CCN([S+](F)F)CC.C([O-])(O)=O.[Na+]>ClCCl>[F:29][CH2:19][CH2:18][C:17]#[C:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[N:8]=[CH:9]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 44517918(Diethylamino)(difluoro)sulfanium tetrafluoroborateHCID 66793408HCID 66793408, compound2×

Product 1

HCID 66793261HCID 66793261, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-3-yn-1-ol (1.0 g, 3.7 mmol; Intermediate 17) in dry dichloromethane (25 mL), was added triethylamine.3HF (1.2 g, 7.4 mmol). XtalFluor-E (1.2 g, 5.5 mmol) was then added. The resulting solution was stirred at room temperature for 30 minutes. Upon completion, the reaction solution was neutralized by slow addition of saturated NaHCO3 (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0-20% EtOAc in petroleum ether) affording the title compound (100 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 1H), 7.88 (s, 1H), 7.73 (d, 1H), 7.42 (dd, 1H), 5.86 (dd, 1H), 4.60 (dt, 2H), 3.88 (m, 1H), 3.78-3.71 (m, 1H), 2.89 (dt, 2H), 2.48-2.34 (m, 1H), 2.06-1.95 (m, 2H), 1.78-1.72 (m, 1H), 1.58 (m, 2H); LCMS: 273 (M+H)+.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (0-20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c61e7d57a14e4e02a3845ce134124e8e
Source dataset
uspto-grants-2012_10
Patent number
US08299112B2

Reaction notes

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