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

HRID 1825783
Notes
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Reaction equation

HRID 1825783 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66052622-Chloro-6-morpholinopyran-4-oneHCID 23574569tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-thioxanthen-2-ylcarbamate

Product 1

HCID 23574574[5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

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

  1. customThe mixture was degassed for 15 minutes
  2. concentrationThe reaction mixture was concentrated in vacuo and water (50 ml)
  3. additionwas added
  4. filtrationThe brown solid was filtered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes