Potassium Phosphate, Tribasic → HCID 45082572, compound

HRID 1877784Notes

Reaction equation

HRID 1877784 reaction equation
I[C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[NH:5][CH:6]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(C(C)=C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO>[CH2:11]=[C:12]([C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[NH:5][CH:6]=1)[CH3:16]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

Product 1

HCID 45082572HCID 45082572, compoundYield 68.79%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

Mix methyl 4-iodo-1H-pyrrole-2-carboxylate (1.5 g, 5.98 mmoles), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (3.01 g, 17.98 mmoles) 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) (0.3 g, 0.06 mmoles), tris(dibenzylideneacetonyl)bis-palladium (Pd2(dba)3) (0.3 g, 0.06 mmoles), tripotassium phosphate (2.54 g, 11.95 mmoles) and methanol (12 mL). Heat the mixture in a sealed tube in a microwave at 140° C. for 30 minutes. Cool, filter the reaction mixture and wash sinter with methanol, evaporate the filtrate under reduced pressure and chromatograph on silica eluting with isohexane/dichloromethane (gradient elution, 100:0 to 0:100). Evaporate the fractions containing product to give methyl 4-(prop-1-en-2-yl)-1H-pyrrole-2-carboxylate. (0.679 g, 68.79% yield). MS (m/z): 166.1 (M+1).

Workup

  1. temperatureCool
  2. filtrationfilter the reaction mixture
  3. washwash sinter with methanol
  4. customevaporate the filtrate under reduced pressure and chromatograph on silica eluting with isohexane/dichloromethane (gradient elution, 100:0 to 0:100)
  5. customEvaporate the fractions
  6. additioncontaining product

Sources & evidence

ORD record
ord-39eccdaf62db43108d864c4d93b08ca9
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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