Water → HCID 69508076, compound

HRID 1767208Notes

Reaction equation

HRID 1767208 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6](B(O)O)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:27][C:28](=[O:42])[C:29]1[C:34]([CH3:35])=[CH:33][CH:32]=[C:31]([C:36]2[CH2:40][CH2:39][CH2:38][C:37]=2Br)[CH:30]=1)[CH3:26].O>C1(C)C(CCO)=CC=CC=1>[CH2:25]([O:27][C:28](=[O:42])[C:29]1[CH:30]=[C:31]([C:36]2[CH2:40][CH:39]=[CH:38][C:37]=2[C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:32]=[CH:33][C:34]=1[CH3:35])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acidHCID 58887641Benzoic acid, 5-(2-bromo-1-cyclopenten-1-yl)-2-methyl-, ethyl ester

Product 1

HCID 69508076HCID 69508076, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 882672-Methylphenethyl alcoholSolvent

Procedure

(5-chloro-2-benzyloxyphenyl)boronic acid (150 mg, 0.5 mmol), Pd(0)[PPh3]4 (25 mg, 0.021 mmol), potassium carbonate (483 mg, 3.36 mmol) and (3-(2-bromo-cyclopent-1-enyl)-6-methylbenzoic acid ethyl ester (130 mg, 0.42 mmol) in toluene-ethanol (1:1 10 mL) were stirred at 90° C., under nitrogen, for 2 hrs. Upon cooling, the reaction mixture was poured into water and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried (MgSO4), filters and concentrated. The residue was purified on a Biotage® using 5% of ethyl acetate in iso-hexane to give the required product as white solid (114 mg, 61%). 1HNMR (CDCl3):1.27(3H,t, J=12 Hz), 2.01–2.08(2H, m), 2.51(3H, s), 2.83(2H, t, J=6 Hz), 2.90(2H, t, J=6 Hz), 4.94(2H, s), 6.80(1H, d, J=Hz), 6.97–7.70 (9H, m), 7.70(1H, s). LC/MS; Rt=4.22 [M+H] 447 (1 Cl)

Workup

  1. temperatureUpon cooling
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4), filters
  4. concentrationconcentrated
  5. customThe residue was purified on a Biotage®

Sources & evidence

ORD record
ord-1b1d8d0727954ffb96e2098d954b4392
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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