Potassium Carbonate → 6-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthrene-2-carboxylic Acid Methyl Ester

HRID 1825812Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3B3OC(C)(C)C(C)(C)O3)[S:8][C:7]=2[CH:6]=1)=[O:4].Cl[C:29]1[O:30][C:31]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][C:33](=[O:35])[CH:34]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:10]3[C:9](=[CH:14][CH:13]=[CH:12][C:11]=3[C:29]3[O:30][C:31]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[CH:32][C:33](=[O:35])[CH:34]=3)[S:8][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-thianthrene-2-carboxylic acid methyl ester (1.1 g, 2.83 mmol), 2-chloro-6-morpholin-4-yl-pyran-4-one (0.73 g, 3.4 mmol) and K2CO3 (0.8 g, 5.66 mmol) were dissolved in dry 1,4-dioxane (7 ml). The mixture was degassed for 15 mins and Pd(PPh3)4 (0.16 g, 5 mol %) was then added The dark brown mixture was heated to 90° C. under an atmosphere of N2 for 24 hour. The reaction mixture was concentrated in vacuo and water (100 ml) was added. The brown solid was filtered and washed with water (1.23 g, 96%). m/z (LC-MS, ESP), RT=4.49 min, (M++1)=454.

Workup

customThe mixture was degassed for 15 mins
additionPd(PPh3)4 (0.16 g, 5 mol %) was then added The dark brown mixture
concentrationThe reaction mixture was concentrated in vacuo and water (100 ml)
additionwas added
filtrationThe brown solid was filtered
washwashed with water (1.23 g, 96%)

Sources & evidence

ORD record: ord-3b56c5779876467189fb5ac62ae9464a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049313B2

Reaction notes

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