Hydrochloric Acid → 3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde

HRID 1177393Notes

Reaction equation

[O:1]1CCCO[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]2([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:31])[CH:8]=1.Cl.O>C1COCC1>[F:31][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:23][CH2:24]1)[N:16]=2)[CH:2]=[O:1]

Participants

Conditions

Temperature: 65 °C

Procedure

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine (22.3 g, 51.6 mmol) in 200 mL THF was added 200 mL 5N HCl. The reaction mixture became warm, was fitted with a water-cooled reflux condenser, and was heated to 65° C. in an oil bath under argon. After 3 h, the reaction was nearly homogeneous. The bath was turned off and the reaction allowed to stir overnight. In the morning a nice yellow precipitate was evident. The THF was removed in vacuo, and the resulting slurry was filtered, rinsing with water, and dried under nitrogen, then dried in vacuo overnight to give 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde as a light orange solid. MS (ESI) m/z: Calculated: 374.1; Observed: 375.1 (M++1).

Workup

temperatureThe reaction mixture became warm
temperaturecooled
temperaturereflux condenser
customThe THF was removed in vacuo
filtrationthe resulting slurry was filtered
washrinsing with water
customdried under nitrogen
customdried in vacuo overnight

Sources & evidence

ORD record: ord-4ee4f0492bb84ba2997e493cd8d76bfc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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