Trifluoromethanesulfonic acid → HCID 117690141, compound

HRID 1502077Notes

Reaction equation

HRID 1502077 reaction equation
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C@H:11]2[O:16][CH2:15][C@@H:14]3[CH2:17][NH:18][CH2:19][CH2:20][N:13]3[CH2:12]2)=[CH:4][CH:3]=1.OS(C(F)(F)F)(=O)=O.C1C(=O)N([I:36])C(=O)C1>>[F:1][C:2]1[C:3]([I:36])=[CH:4][C:5]([C@H:11]2[O:16][CH2:15][C@@H:14]3[CH2:17][NH:18][CH2:19][CH2:20][N:13]3[CH2:12]2)=[C:6]([CH3:10])[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 71273534HCID 71273534, compound

Product 1

HCID 117690141HCID 117690141, compound

Procedure

6-fluoro-2-methyl-3-((3R,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrile (600 mg, 2.18 mmol) was dissolved in triflic acid (5.80 mL, 65.4 mmol), and NIS (1226 mg, 5.45 mmol) was added at 0° C. The reaction mixture was stirred at rt overnight and quenched into ice water and basified with 5 N NaOH. The aqueous layer was extracted with DCM. The organic layer was washed with aqueous NaS2O3, NaHCO3, brine, dried and evaporated to give crude title compound, which was used without further purification. LC/MS: [(M+1)]+=402.1;

Workup

  1. customquenched into ice water and basified with 5 N NaOH
  2. extractionThe aqueous layer was extracted with DCM
  3. washThe organic layer was washed with aqueous NaS2O3, NaHCO3, brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b1e227e79d1c449a922fa2be86e3e705
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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