Sodium Carbonate → HCID 90417938, compound

HRID 2177226Notes

Reaction equation

HRID 2177226 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12](I)[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[CH3:20][C:21]1(C)[C:25](C)(C)OB(C(C)=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC.O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:21]([CH3:25])=[CH2:20])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 90418750HCID 90418750, compound

Product 1

HCID 90417938HCID 90417938, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

Into a 25-mL round-bottom flask, was placed ethyl 3-(4-ethylphenyl)-5-iodo-1,2-thiazole-4-carboxylate (200 mg, 0.52 mmol, 1.00 equiv), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (130.24 mg, 0.78 mmol, 1.50 equiv), sodium carbonate (164.34 mg, 1.55 mmol, 3.00 equiv), Pd(dppf)Cl2 (37.82 mg, 0.05 mmol, 0.10 equiv), DME/H2O (6 mL). The resulting solution was stirred for 16 h at 95° C. in an oil bath under nitrogen. The resulting solution was extracted with 150 mL of dichloromethane. The organic layer was washed with 1×30 mL of brine, dried over anhydrous sodium sulfate and concentrated. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20). This resulted in 287.4 mg of ethyl 3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazole-4-carboxylate as brown oil. Mass spectrum (ESI, m/z): Calcd. for C12H19NO2S, 302.4 (M+H). found 302.4.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 150 mL of dichloromethane
  3. washThe organic layer was washed with 1×30 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate/petroleum ether (1:20)
  7. customThis resulted in 287.4 mg of ethyl 3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazole-4-carboxylate as brown oil

Sources & evidence

ORD record
ord-0e8a0dd9f8e0439e9413eaa968d689ab
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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