Bromide ion → HCID 59299909, compound

HRID 2236505Notes

Reaction equation

HRID 2236505 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C[Si]([N-:42][Si](C)(C)C)(C)C.[K+].[Br-]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([NH2:42])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 259Bromide ionHCID 6212ChloroformHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59299825HCID 59299825, compound

Product 1

HCID 59299909HCID 59299909, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-Bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (400 mg, 1.18 mmol) in toluene (4 mL) is added Pd2(dba)3.CHCl3 (50 mg, 0.05 mmol) and P(tBu)3 (40 mg, 0.20 mmol). The mixture is degassed at −30° C. KHMDS (7.0 mL, 0.5 M solution in toluene, 3.5 mmol)) is added to the flask. The resulting mixture is stirred at room temperature overnight. TLC is used to detect when the starting bromide is consumed, the reaction mixture is diluted with ether and poured into dilute HCl (aq). The ether layer is discarded, the aqueous layer is basified with NH4OH and extracted with CH2Cl2. The CH2Cl2 layer is dried and concentrated. The residue (300 mg) is directly employed in the next step.

Workup

  1. customThe mixture is degassed at −30° C
  2. customis consumed
  3. additionthe reaction mixture is diluted with ether
  4. additionpoured into dilute HCl (aq)
  5. extractionextracted with CH2Cl2
  6. dry with materialThe CH2Cl2 layer is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b192fc90edaf4645ab2e047fe7ed260d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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