5-Bromosalicylaldehyde → HCID 23508725, compound

HRID 1883949Notes

Reaction equation

HRID 1883949 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:16]=[CH:17][C:18]([OH:23])=[C:19]([CH:22]=1)[CH:20]=[O:21].[CH2:24]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[Na+]>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].O.C1(C)C=CC=CC=1>[CH2:24]([N:31]1[CH2:36][CH2:35][N:34]([C:15]2[CH:16]=[CH:17][C:18]([OH:23])=[C:19]([CH:22]=2)[CH:20]=[O:21])[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 728635-BromosalicylaldehydeHCID 759941-BenzylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 23508725HCID 23508725, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.6 g of bis(dibenzylideneacetone)palladium and 0.16 g of tri-tert-butylphosphine are added under nitrogen to 200 ml of toluene, and the resultant dark-red solution is stirred at 20° for 20 minutes. 10 g of 5-bromo-2-hydroxybenzaldehyde, 9.7 g of 1-benzylpiperazine and 7.2 g of sodium tert-butoxide are then added. The mixture is stirred at 60° for 24 hours and cooled, 800 ml of water are added, and the mixture is extracted with 2×500 ml of ethyl acetate. The organic phases are combined and washed with 300 ml of water, and the solvent is removed at 30° under reduced pressure. The dark-orange oil which remains (9.7 g) is purified by chromatography (300 g of silica gel; MTB ether/heptane 5:1; 1.5 litres). 9.9 g of pale-yellow crystals remain (67%), m.p. 101-103°; MS 296 (M+), 205, 119, 91 (100%).

Workup

  1. stirringThe mixture is stirred at 60° for 24 hours
  2. temperaturecooled
  3. extractionthe mixture is extracted with 2×500 ml of ethyl acetate
  4. washwashed with 300 ml of water
  5. customthe solvent is removed at 30° under reduced pressure
  6. customis purified by chromatography (300 g of silica gel; MTB ether/heptane 5:1; 1.5 litres)

Sources & evidence

ORD record
ord-e4de81c355504c49bfdd45de0054b84a
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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