2-(3-Bromophenyl)-1,3-dioxolane → HCID 11772109, compound

HRID 1765449Notes

Reaction equation

HRID 1765449 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]3[O:12][CH2:11][CH2:10][O:9]3)[CH:3]=2)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 4158521-Benzyl-4-piperidylamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 11772109HCID 11772109, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a dry flask containing 2-(3-bromophenyl)-1,3-dioxaolane (1.0 mL; 1.0 eq) and amine 6, (1.6 mL; 1.2 eq) in dry toluene (20 mL) was added BINAP (124 mg; 0.03 eq), palladium acetate (30 mg; 0.02 eq) and sodium tert-butoxide (0.89 g; 1.4 eq). The reaction was heated to 80° C. under nitrogen. After 2 hours the solution was cooled, diluted with ethyl acetate and washed with one portion water. The organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 5% methanol in dichloromethane. An orange oil was obtained (2.035 g; 91% yield).

Workup

  1. temperatureAfter 2 hours the solution was cooled
  2. washwashed with one portion water
  3. dry with materialThe organics were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% methanol in dichloromethane
  8. customAn orange oil was obtained (2.035 g; 91% yield)

Sources & evidence

ORD record
ord-d842f169ed3d40c983a66c01fff306ef
Source dataset
uspto-grants-2007_06
Patent number
US07226933B2

Reaction notes

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