HCID 18367277, compound → HCID 18367330, compound

HRID 1741405Notes

Reaction equation

HRID 1741405 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]([NH:20][CH:21]3[C:30]4[C:25](=[C:26]([O:31]C)[CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)[CH3:19])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]([NH:20][CH:21]3[C:30]4[C:25](=[C:26]([OH:31])[CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23][CH2:22]3)[CH3:19])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 18367277HCID 18367277, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 18367330HCID 18367330, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-methoxynaphthalene (0.33 g) in CH2Cl2 (7 ml) was added 1M BBr3 -CH2Cl2 solution (1.5 ml) at 0° C. After being stirred for 3 hours at the same temperature, the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with water and brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[1-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.23 g). MS (m/z): 411 (M+ +1) NMR (CDCl3, δ): 1.57 (3H, d, J=6.8 Hz), 1.64-2.20 (4H, m), 2.44-2.86 (2H, m), 3.89 (0.5H, m), 4.12 (0.5H, q, J=6.8 Hz), 4.29 (0.5H, q, J=6.8 Hz), 4.78 (0.5H, m), 6.62-6.72 (1H, m), 6.97-7.14 (2H, m), 7.32-7.41 (6H, m), 7.58-7.68 (4H, m)

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and sat. NaHCO3
  3. washThe organic layer was washed with water and brine
  4. customThe dried solvent was evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cde7a09962d14c5c8bc11238b3e94311
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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