Phenylboronic Acid → HCID 68889039, compound

HRID 1292947Notes

Reaction equation

HRID 1292947 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[NH:7][CH:8]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][N:9]32)=[CH:4][CH:3]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:23]=[C:6]1[C:5]2[C:10](=[CH:11][C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:3][CH:4]=2)[N:9]2[CH2:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:8]2[NH:7]1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 68890173HCID 68890173, compound

Product 1

HCID 68889039HCID 68889039, compoundYield 45.6%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the part A compound from Example 3 (100 mg, 0.26 mmol), phenyl boronic acid (48 mg, 0.39 mmol), a solution of aqueous 2.0 M sodium bicarbonate (380 μl, 0.76 mmol) and tetrakis(triphenylphosphine) palladium(0) (1 mg, 0.86 μmol) in degassed DME (1.5 mL) was heated at 90° C. for 18 h under nitrogen. The mixture was diluted with ethyl acetate (20 mL), washed with a solution of aqueous saturated sodium bicarbonate (3×20 mL), dried over sodium sulfate and concentrated. The crude product was purified by ISCO flash chromatography (silica gel/hexane-ethyl acetate 100:0 to 0:100 gradient) to afford the title compound as a white solid (45 mg, 45% yield).

Workup

  1. washwashed with a solution of aqueous saturated sodium bicarbonate (3×20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by ISCO flash chromatography (silica gel/hexane-ethyl acetate 100:0 to 0:100 gradient)

Sources & evidence

ORD record
ord-109aff2af4c844478d96c56ff7b86f0a
Source dataset
uspto-grants-2007_07
Patent number
US07238702B2

Reaction notes

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