(Diethylamino)sulfur trifluoride → HCID 68181728, compound

HRID 1398612Notes

Reaction equation

HRID 1398612 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=3)[C:10]([C:18](O)([CH3:20])[CH3:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:17][C:14]1[CH:15]=[C:16]2[C:11]([C:10]([C:18]([F:28])([CH3:20])[CH3:19])=[N:9][N:8]2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68181837HCID 68181837, compound

Product 1

HCID 68181728HCID 68181728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-indazol-3-yl]propan-2-ol (200 mg, 0.57 mmol) in dry DCM (2 mL) at 0° C. under an atmosphere of nitrogen was introduced (diethylamino)sulphur trifluoride (0.14 mL, 1.15 mmol). The reaction was left to warm to RT for 1 hr. Following addition of sodium bicarbonate (5 mL of a saturated aqueous solution), the reaction mixture was washed with DCM (2×5 mL), and the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage, eluent heptane:EtOAc [0-100%] gradient) to furnish the title compound as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 1.81-1.97 (6H, m), 5.18 (2H, br. s.), 7.28 (1H, s), 7.40-7.50 (1H, m), 7.78-7.92 (1H, m), 8.32 (1H, d, J=5.67 Hz), 9.01 (1H, d, J=1.10 Hz); LC-MS: m/z=+349.95/351.80 (M+H)+.

Workup

  1. waitThe reaction was left
  2. washthe reaction mixture was washed with DCM (2×5 mL)
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (Biotage, eluent heptane:EtOAc [0-100%] gradient)

Sources & evidence

ORD record
ord-b98c13ed1ad542dbab22009157983fcd
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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