1,2-Dimethoxyethane → HCID 90418030, compound

HRID 2177234Notes

Reaction equation

HRID 2177234 reaction equation
COCCOC.[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18](I)[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.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].O>[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 90418750HCID 90418750, compound

Product 1

HCID 90418030HCID 90418030, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Into a 8-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethylene glycol dimethyl ether (2 mL), water (1 mL), ethyl 3-(4-ethylphenyl)-5-iodo-1,2-thiazole-4-carboxylate (50 mg, 0.13 mmol, 1.00 equiv), phenylboronic acid (18.9 mg, 0.16 mmol, 1.20 equiv), Pd(dppf)Cl2 (5.2 mg, 0.01 mmol, 0.06 equiv), sodium carbonate (41 mg, 0.39 mmol, 3.00 equiv). The resulting solution was stirred for 2 h at 90° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20). The collected fractions were combined and concentrated under vacuum. This resulted in 56 mg of ethyl 3-(4-ethylphenyl)-5-phenyl-1,2-thiazole-4-carboxylate as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C20H19NO2S, 338.1 (M+H). found 338.1.

Workup

  1. customInto a 8-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. washeluted with ethyl acetate/petroleum ether (1:20)
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 56 mg of ethyl 3-(4-ethylphenyl)-5-phenyl-1,2-thiazole-4-carboxylate as yellow oil

Sources & evidence

ORD record
ord-c7dabd25736f480ab3fb0df29330581c
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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