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Potassium Phosphate, Tribasic → Ethyl 3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazole-4-carboxylate

HRID 2177404
Notes
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Reaction equation

HRID 2177404 reaction equation
[Cl:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5](Cl)[S:4][N:3]=1.[CH3:13][CH:14]1[CH2:19][CH2:18][C:17](B(O)O)=[CH:16][CH2:15]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[Cl:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([C:17]2[CH2:18][CH2:19][CH:14]([CH3:13])[CH2:15][CH:16]=2)[S:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 441195564-Methylcyclohexen-1-ylboronic acidHCID 90418456Ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate

Product 1

HCID 118184949Ethyl 3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazole-4-carboxylateYield 63.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed ethyl 3,5-dichloro-1,2-thiazole-4-carboxylate (150 mg, 0.66 mmol, 1.00 equiv), (4-methylcyclohex-1-en-1-yl)boronic acid (103 mg, 0.74 mmol, 1.11 equiv), Pd(PPh3)4 (38 mg, 0.03 mmol, 0.05 equiv), K3PO4 (368 mg, 1.73 mmol, 2.61 equiv), dioxane (3 mL). The resulting solution was stirred overnight at 90° C. in an oil bath. The solids were removed by filtration. The resulting mixture was concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (2:98) to afford 120 mg (63%) of ethyl 3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazole-4-carboxylate as a colorless oil.

Workup

  1. customInto a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe solids were removed by filtration
  4. concentrationThe resulting mixture was concentrated under reduced pressure
  5. washeluting with ethyl acetate/petroleum ether (2:98)

Sources & evidence

ORD record
ord-0aebdce638564bde939d34ba08dd6a63
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09067898B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes