(Diethylamino)sulfur trifluoride → HCID 68283963, compound

HRID 1630629Notes

Reaction equation

HRID 1630629 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)(O)[CH3:14])[C:7]3[CH2:22][CH2:23][N:24]([CH3:26])[CH2:25][C:6]=3[C:5]=2[CH:4]=1.C(N(S(F)(F)[F:33])CC)C>C(Cl)Cl>[F:33][C:13]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)([CH3:14])[CH2:12][N:8]1[C:9]2[CH:10]=[CH:11][C:3]([CH2:2][OH:1])=[CH:4][C:5]=2[C:6]2[CH2:25][N:24]([CH3:26])[CH2:23][CH2:22][C:7]1=2

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 60197675HCID 60197675, compound

Product 1

HCID 68283963HCID 68283963, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(8-Hydroxymethyl-2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-3-yl-propan-2-ol (700 mg, 1.99 mmol) was dissolved in 70 mL DCM and cooled to 0° C. Diethylaminosulfur trifluoride (800 mg, 4.9 mmol) in DCM (5 mL) was added dropwise at the same temperature and stirred for 45 min. The reaction was monitored by TLC and LCMS. After consumption of starting material, the reaction mixture was quenched with saturated bicarbonate and extracted with DCM. The organic layer was washed with water and brine solution, dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by reverse phase chromatography to obtain 14 mg of [5-(2-fluoro-2-pyridin-3-yl-propyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl]-methanol. 1H NMR (CDCl3, freebase) δ (ppm): 8.6 (s, 1H), 8.57 (d, 1H), 7.6 (d, 1H), 7.35 (s, 1H), 7.2 (m, 1H), 7.125 (m, 2H), 4.72 (s, 2H), 4.3 (m, 2H), 3.6 (q, 2H), 2.8 (m, 1H), 2.7 (dd, 2H), 2.6 (m, 1H), 2.52 (s, 3H), 1.75 (d, 3H). Separation by chiral HPLC provides enantiomers II-213a-b.

Workup

  1. customAfter consumption of starting material
  2. customthe reaction mixture was quenched with saturated bicarbonate
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-57574f47bea945c59c25eb8b63ddcbcc
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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