Sodium Hydroxide → 3-Fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177434Notes

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:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:34])[CH:8]=1.[OH-].[Na+]>C1COCC1>[F:34][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:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[N:16]=2)[CH:2]=[O:1]

Participants

Conditions

Temperature: 80 °C

Procedure

A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine (0.467 g, 0.984 mmol) in 5 mL 1:1 THF/5N HCl was sealed and heated to 80° C. The resulting yellow solution was allowed to stir 3 h, was cooled, and then was treated with ice and 10N NaOH until basic. The reaction mixture was partitioned between EA and water, washed with water, brine, dried over sodium sulfate, filter, concentrate in vacuo to give 3-fluoro-4-(5-(1-phenylcyclohexyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde as an oil/solid that contained some starting material. This material was carried on without further pyrification. MS (ESI) m/z: Calculated: 416.1; Observed: 417.1 (M++1).

Workup

temperaturewas cooled
customThe reaction mixture was partitioned between EA and water
washwashed with water, brine
dry with materialdried over sodium sulfate
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-37faf0cc30e4438db0bb53091cb60d56
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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