(Diethylamino)sulfur trifluoride → HCID 71295560, compound

HRID 1776844Notes

Reaction equation

HRID 1776844 reaction equation
CCN(S(F)(F)[F:7])CC.[Br:10][C:11]1[CH:30]=[CH:29][C:14]2[O:15][CH2:16][CH:17](O)[CH2:18][N:19]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:21]=[C:20]3[C:13]=2[CH:12]=1>C(Cl)Cl.O>[Br:10][C:11]1[CH:30]=[CH:29][C:14]2[O:15][CH2:16][CH:17]([F:7])[CH2:18][N:19]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:21]=[C:20]3[C:13]=2[CH:12]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71295661HCID 71295661, compound

Product 1

HCID 71295560HCID 71295560, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

DAST (94 mg, 0.583 mmol) was added to a solution of 2-bromo-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-ol (100 mg, 0.29 mmol) in CH2Cl2 (1 mL) under N2 at −78° C. The mixture was stirred at room temperature for 2 hours. The mixture was then diluted with water (30 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was washed with brine (20 mL×2), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using p-TLC (petroleum ether:EA=10:1) to provide 2-bromo-7-fluoro-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indole (40 mg, yield: 40.0%). MS (M+H)+: 346/348.

Workup

  1. extractionextracted with ethyl acetate (15 mL×3)
  2. washThe organic layer was washed with brine (20 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-bc3e0ccabfd646b8b77937c9a813d038
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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