Hydrochloric Acid → HCID 10150878, compound

HRID 1836031Notes

Reaction equation

HRID 1836031 reaction equation
Br[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=2[CH:13]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>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.CCO>[CH2:9]([O:10][C:11]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=2[C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=3[CH:13]=2)=[CH:14][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 10236546HCID 10236546, compound

Product 1

HCID 10150878HCID 10150878, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Compound 102 (0.23 g, 7.9 mmol) in a solution consisting of Tol/EtOH/2M Na2CO3 aq (15 mL/2 mL/15 mL) was treated with 4-benzloxy phenylboronic acid (0.12 g, 1.0 mmol) and cat Pd(PPh3)4 and heated to reflux until TLC analysis indicated complete reaction. The reaction mixture was treated with 2 N HCl aq and extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3 aq, brine and dried over MgSO4. After filtration, the residue was chromatographed on silica gel (1:4 EtOAc/hexanes) to yield the desired product as an orange solid. The orange solid thus obtained was triturated with CH2Cl2 to yield the pdt (2.4 g) as a white solid: Mp=186-187° C.; 1H NMR (DMSO-d6) δ 9.90 (br s, 1 H), 9.05 (br s, 1 H), 7.65 (d, 1 H, J=8.5 Hz), 7.51-7.31 (m, 5 H), 7.19 (d, 1 H, J=8.5 Hz), 7.17 (d, 2 H, J=8.6 Hz), 7.02 (d, 2 H, J=8.7 Hz), 6.86 (dd, 1 H, J=8.5 Hz, 2.4 Hz), 6.70 (d, 2 H, J=1.8 Hz), 6.63 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 5.86 (s, 1 H), 5.14 (s, 2 H); MS 407 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureto reflux until TLC analysis
  3. customreaction
  4. extractionextracted with EtOAc
  5. washThe EtOAc layer was washed with saturated NaHCO3 aq, brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration
  8. customthe residue was chromatographed on silica gel (1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-4ed9d544ad644945a1c1d53b2bd515a3
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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