Ozone → (2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanone

HRID 1177437Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=C)[N:16]=3)=[C:9]([F:30])[CH:8]=1.[O:31]=[O+][O-]>C(Cl)Cl.CO>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:31])[N:16]=3)=[C:9]([F:30])[CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine (2.66 g, 6.4 mmol) in 3:1 CH2Cl2/MeOH (128 mL) at −78° C. was treated with ozone for 15 min. The solution was then sparged with O2, dimethyl sulfide (18 mL) was added, and the bath was allowed to expire. The resulting solution was stirred at 25° C. for 3 d and then concentrated in vacuo. This residue was taken up in CH2Cl2 (400 mL) and sequentially washed with water and brine, then concentrated in vacuo to provide (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(phenyl)methanone as a yellow solid. MS (ESI) m/z: Calculated: 420.1; Observed: 421.1 (M++1).

Workup

customThe solution was then sparged with O2, dimethyl sulfide (18 mL)
additionwas added
concentrationconcentrated in vacuo
washsequentially washed with water and brine
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-35a939e66b454657a497732406409882
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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