2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine → 4-(5-(1-(4-(Benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde

HRID 1177495Notes

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][C:28]([O:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:27][CH:26]=4)[CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:39])[CH:8]=1>C1COCC1.Cl>[CH2:32]([O:31][C:28]1[CH:27]=[CH:26][C:25]([C:22]2([C:17]3[N:16]=[C:15]4[S:14][C:13]([C:10]5[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[CH:8][C:9]=5[F:39])=[N:21][C:20]4=[CH:19][CH:18]=3)[CH2:23][CH2:24]2)=[CH:30][CH:29]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)-phenyl)cyclopropyl)thiazolo[5,4-b]pyridine (0.305 g, 0.566 mmol) in 5 mL THF and 5 mL 5N aq. HCl was heated in a sealed vial to 65° C. for 1 h. The reaction mixture was cooled, poured onto ice, quenched with 10 N NaOH, sonicated in 5 mL MTBE, filtered, and rinsed with 1 mL MTBE. The solid was collected to give 4-(5-(1-(4-(benzyloxy)-phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as an orange solid. MS (ESI) m/z: calculated: 480.1; Observed: 481.1 (M++1).

Workup

temperatureThe reaction mixture was cooled
additionpoured onto ice
customquenched with 10 N NaOH
customsonicated in 5 mL MTBE
filtrationfiltered
washrinsed with 1 mL MTBE
customThe solid was collected

Sources & evidence

ORD record: ord-2df8b4b83be44e0498bcd25d2bc61d00
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

Loading…