Hydrogen Bromide → HCID 86761674, compound

HRID 1875340Notes

Reaction equation

HRID 1875340 reaction equation
Br[C:2]1[S:12][C:5]2[CH:6]([CH3:11])[N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[CH:3]=1.Br.[C:14]([O-:17])(=[O:16])C.[Na+].[CH2:19](N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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].CO>[CH3:10][N:7]1[CH2:8][CH2:9][C:4]2[CH:3]=[C:2]([C:14]([O:17][CH3:19])=[O:16])[S:12][C:5]=2[CH:6]1[CH3:11]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 517045Sodium AcetateHCID 68590368HCID 68590368, compound

Product 1

HCID 86761674HCID 86761674, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.0 g (6.1 mmol) (RS)-2-bromo-6,7-dimethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine×HBr, 2.0 g (24 mmol) sodium acetate and 100 ml of methanol is combined with 15 mg (0.067 mmol) palladium acetate, 150 mg (0.27 mmol) 1,1′-bis(diphenylphosphino)ferrocene and 2.6 ml (18 mmol) triethylamine and carbonylated for 3.5 h at 80° C. under 5 bar of CO atmosphere. Then the mixture is filtered off, concentrated, combined with sat. NaHCO3 solution and methylene chloride and the resulting emulsion is filtered through Celite. The aqueous phase is separated off and extracted 2× with methylene chloride and the combined organic phases are dried with Na2SO4 and concentrated. The crude product is reacted further without any further purification.

Workup

  1. filtrationThen the mixture is filtered off
  2. concentrationconcentrated
  3. filtrationthe resulting emulsion is filtered through Celite
  4. customThe aqueous phase is separated off
  5. extractionextracted 2× with methylene chloride
  6. dry with materialthe combined organic phases are dried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is reacted further without any further purification

Sources & evidence

ORD record
ord-b0b780a4ee364356a9650cfec1c7a5fd
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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