Water → HCID 66742968, compound

HRID 1431215Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[CH2:14]O)[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2.C(N(S(F)(F)[F:24])CC)C.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[CH2:14][F:24])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2

Participants

Conditions

Temperature: -78 °C

Procedure

8-fluoro-6-(1-hydroxy-2-methylpropan-2-yl)isoquinolin-1(2H)-one (114 mg, 485 μmol) was dissolved in DCM (dry) and cooled to −78° C. under argon. To this solution was added the diethylaminosulfur trifluoride (90 μl, 678 μmol) and the reaction was stirred for about 10 min before removal of the cooling bath. The reaction was warmed to ambient and stirred at this temperature for 2 hrs. To the reaction mixture was added 25 ml water and 20 ml DCM. The mixture was shaken and the organics collected. The organics were washed with 25 ml brine. The aqueous phase was extracted (2×20 ml DCM). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by preparative tlc (2 plates, eluted with 4.5% MeOH/DCM) to afford 92 mg of the desired product as an off-white powder. (M+H)+=238 m/e.

Workup

temperatureThe reaction was warmed to ambient and
stirringstirred at this temperature for 2 hrs
stirringThe mixture was shaken
washThe organics were washed with 25 ml brine
extractionThe aqueous phase was extracted (2×20 ml DCM)
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by preparative tlc (2 plates, eluted with 4.5% MeOH/DCM)

Sources & evidence

ORD record: ord-742c7363b5074dc5b0c90a77d1252876
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940741B2

Reaction notes

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