Potassium Carbonate → [5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yl]-carbamic acid tert-butyl ester

HRID 1825783Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3B3OC(C)(C)C(C)(C)O3)[CH2:11][C:10]=2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:33]1[O:34][C:35]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[CH:36][C:37](=[O:39])[CH:38]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:33]3[O:34][C:35]([N:40]4[CH2:41][CH2:42][O:43][CH2:44][CH2:45]4)=[CH:36][C:37](=[O:39])[CH:38]=3)[CH2:11][C:10]=2[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-thioxanthen-2-yl]-carbamic acid tert-butyl ester (1.02 g, 2.32 mmol), 2-chloro-6-morpholin-4-yl-pyran-4-one (3) (0.60 g, 2.78 mmol) and K2CO3 (0.64 g, 4.64 mmol) were dissolved in dry 1,4-dioxane (ml). The mixture was degassed for 15 minutes and Pd(PPh3)4 (0.13 g, 0.12mol) 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 (50 ml) was added. The brown solid was filtered and washed with water (1.21 g, 88%). m/z (LC-MS, ESP), RT=4.6 minutes, (M++1)=493.

Workup

customThe mixture was degassed for 15 minutes
concentrationThe reaction mixture was concentrated in vacuo and water (50 ml)
additionwas added
filtrationThe brown solid was filtered
washwashed with water (1.21 g, 88%)

Sources & evidence

ORD record: ord-4a929c2deae34c8aa205a88be00d1e47
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049313B2

Reaction notes

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