1,2-Dimethoxyethane → HCID 68524427, compound

HRID 1990098Notes

Reaction equation

HRID 1990098 reaction equation
CO[CH2:3][CH2:4]OC.CC1(C)C(C)(C)OB(C2C=CC([C:21]3[N:25]=[CH:24][S:23][N:22]=3)=CC=2)O1.[CH2:27]([O:29][C:30]([C:32]1[S:33][C:34]([CH2:40][CH3:41])=[C:35]([C:38]#[N:39])[C:36]=1I)=[O:31])[CH3:28].[F-].[Cs+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C>[CH2:27]([O:29][C:30]([C:32]1[S:33][C:34]([CH2:40][CH3:41])=[C:35]([C:38]#[N:39])[C:36]=1[C:4]1[CH:3]=[CH:35][C:36]([N:22]2[CH2:21][N:25]=[CH:24][S:23]2)=[CH:32][CH:30]=1)=[O:31])[CH3:28]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 57975284HCID 57975284, compoundHCID 68522039HCID 68522039, compound

Product 1

HCID 68524427HCID 68524427, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Add DME (3 mL) to a mixture of 3-[4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[1,2,4]thiadiazole (0.066 g, 0.23 mmol), 4-Cyano-3-iodo-5-ethyl-thiophene-2-carboxylic acid ethyl ester (0.071 g, 0.20 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride (1:1) dichloromethane complex (0.009 g, 0.01 mmol) and cesium fluoride (0.103 g, 0.68 mmol) under nitrogen and stir at 80° C. for 3 h. Cool down and add ice-water and ethyl acetate. Separate layers and wash the organic layer with water (3×) and back-extract the combined aqueous layers with ethyl acetate (2×). Wash the combined organic layers with brine, dry over anhydrous sodium sulfate and concentrate under reduced pressure over Celite®. Purify by flash chromatography (silica gel) eluting with hexanes-ethyl acetate 10:1 first, then 5:1 to give 0.06 g of the title compound as a white solid. Mass spectrum ESI positive (m/z): 370 (M+1).

Workup

  1. temperatureCool down and
  2. washSeparate layers and wash the organic layer with water (3×)
  3. extractionback-extract the combined aqueous layers with ethyl acetate (2×)
  4. washWash the combined organic layers with brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationconcentrate under reduced pressure over Celite®
  7. customPurify by flash chromatography (silica gel)
  8. washeluting with hexanes-ethyl acetate 10:1 first

Sources & evidence

ORD record
ord-cc1e4d89f31d462e8e1b681362232f6e
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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