Sodium Carbonate → HCID 18947034, compound

HRID 1769083Notes

Reaction equation

HRID 1769083 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:35][C:36]1[S:37][C:38](Br)=[C:39]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41][C:40]=12>C1(C)C=CC=CC=1>[Br:35][C:36]1[S:37][C:38]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:39]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41][C:40]=12

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 18947041HCID 18947041, compound

Product 1

HCID 18947034HCID 18947034, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.91 g (7.5 mmol) of phenylboronic acid, 0.209 g (0.38 mmol) of (dibenzylideneacetone)-palladium(O), 0,397 g (1.5 mmol) of triphenylphosphine and 7.5 ml (15 mmol) of a 2M sodium carbonate solution are added to a solution of 3.2 g (8.3 mmol) of 1,3-dibromo-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole in 45 ml of toluene. The mixture is heated at reflux for 5.5 hours and then cooled. The organic phase is separated by settling, washed with water, dried over magnesium sulphate and then evaporated to dryness. The residue is purified by chromatography on silica gel using the 5/95 ethyl acetate/hexane eluent mixture. There is obtained 0.98 g of a white solid. Yield 34%. Melting point: 139°-140° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 5.5 hours
  3. temperaturecooled
  4. customThe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel using the 5/95 ethyl acetate/hexane eluent mixture

Sources & evidence

ORD record
ord-d7bf7d83b83143b3bec8bb6011341012
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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