2-(Tri-n-butylstannyl)thiophene → HCID 68427849, compound

HRID 642572Notes

Reaction equation

HRID 642572 reaction equation
C(O[C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[CH2:12][N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])C.C([Sn](CCCC)(CCCC)[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1)CCC>CN(C=O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:4]([C:6]1[S:10][C:9]([C:38]2[S:37][CH:36]=[CH:40][CH:39]=2)=[N:8][C:7]=1[CH2:12][N:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:19]

Participants

6

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 684264542-Bromo-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 68427849HCID 68427849, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-Bromo-4-{[(2,4-dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-thiazole-5-carboxylic acid ethyl ester (1 g, 2 mmol, example 96(b), 2-(tributylstannyl)thiophene (1.26 mL, 2 mmol), dichlorobis(triphenylphosphine)palladium II (140 mg, 0.2 mmol) in 13 mL anhydrous DMF was heated to 130° C. for 20 min. The reaction mixture was cooled, diluted with ethyl acetate, and washed successively with water, saturated sodium bicarbonate, and brine. The organic fraction was dried over anhydrous sodium sulfate, concentrated to a crude residue and purified by column chromatography (eluting from silica gel with a gradient of 15-70% ethyl acetate in hexanes) to give 867 mg of a yellow oil. MS (ESI+): m/z 527.2 (M+23)

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed successively with water, saturated sodium bicarbonate, and brine
  3. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to a crude residue
  5. custompurified by column chromatography (
  6. washeluting from silica gel with a gradient of 15-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0bdb8c87a7c54f71a3593b5a1e1d640d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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