Sodium Carbonate → HCID 70167226, compound

HRID 2188209Notes

Reaction equation

HRID 2188209 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18]([CH2:25][NH:26][CH2:27][C@H:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33](S(C(F)(F)F)(=O)=O)[CH:34]=2)[C@H:29]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[CH2:18]([CH2:25][NH:26][CH2:27][C@H:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:34]=2)[C@H:29]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 70166394HCID 70166394, compound

Product 1

HCID 70167226HCID 70167226, compoundYield 46.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Benzene boronic acid (301 mg), tetrakis(triphenylphosphine)palladium(0) (65 mg), lithium chloride (238 mg) and aqueous sodium carbonate solution (2 M, 2.25 cm3) were added to a stirred solution of cis-2-(N-benzylmethylamino)methyl-6-trifluoromethanesulfonyl-1-phenyl-1,2,3,4-tetrahydronaphthalene (1.1 g) in 1,2-dimethoxyethane (60 cm3) under an atmosphere of nitrogen. The stirred mixture was heated at 90° C. for 46 h before being allowed to cool to room temperature. Water (100 cm3) and ethyl acetate (100 cm3) were added and the organic layer was washed with water (3×100 cm3), dried (Na2SO4), and the solvent was removed under reduced pressure. The crude product (908 mg) was purified by column chromatography [silica, eluting with toluene-ethyl acetate (19:1)] to afford the title compound as a gum (452 mg); positive ion ESI (M+H)+ 417.9.

Workup

  1. temperatureto cool to room temperature
  2. washthe organic layer was washed with water (3×100 cm3)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product (908 mg) was purified by column chromatography [silica, eluting with toluene-ethyl acetate (19:1)]

Sources & evidence

ORD record
ord-c031f89cbfab4cc69f56eeeea7ce4775
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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