Oxane-4-carbonyl chloride → (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridine-5-yl)(tetrahydro-2H-pyran-4-yl)methanone

HRID 1177530Notes

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]([Sn](C)(C)C)[N:16]=3)=[C:9]([F:26])[CH:8]=1.[O:27]1[CH2:32][CH2:31][CH:30]([C:33](Cl)=[O:34])[CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[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:33]([CH:30]2[CH2:31][CH2:32][O:27][CH2:28][CH2:29]2)=[O:34])[N:16]=3)=[C:9]([F:26])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)-thiazolo[5,4-b]pyridine (1.00 g, 2.087 mmol) and tetrahydro-2H-pyran-4-carbonyl chloride (0.434 mL, 2.92 mmol) in 15 mL toluene was sealed and heated to 80° C. After 4 h a precipitate formed. The reaction mixture was cooled and filtered, rinsing with Et2O, and the solid was dried in vacuo to give (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-thiazolo[5,4-b]pyridine-5-yl)(tetrahydro-2H-pyran-4-yl)methanone as a white solid. MS (ESI) m/z: Calculated: 428.1; Observed: 428.8 (M++1).

Workup

customAfter 4 h a precipitate formed
temperatureThe reaction mixture was cooled
filtrationfiltered
washrinsing with Et2O
customthe solid was dried in vacuo

Sources & evidence

ORD record: ord-005ce1bafccc4388ba809221e09c189f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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