Triethylamine → HCID 131732449, compound

HRID 1850030Notes

Reaction equation

HRID 1850030 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([B:12]1[O:20][C:17]([CH3:19])([CH3:18])[C:14]([CH3:16])([CH3:15])[O:13]1)[CH:6]=[CH:5]2.CCN([CH2:26][CH3:27])CC>C(Cl)Cl>[O:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([B:12]1[O:20][C:17]([CH3:19])([CH3:18])[C:14]([CH3:15])([CH3:16])[O:13]1)[CH:6]=[CH:5]2)[C:27]1[CH:26]=[CH:10][CH:11]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 219239636-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol

Product 1

HCID 131732449HCID 131732449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylboronic acid (140 mg, 1.1 mmol, 2.0 eq.) was coevaporated with PhMc twice to produce the anhydride. This was treated with crude 6-hydroxynaphthalene-2-boronic acid pinacol ester (150 mg, 0.56 mmol), DCM (5 mL), NEt3 (400 uL, 3 mmol, 5 eq.), and cupric acetate (100 mg, 0.53 mmol, 0.95 eq.) and stirred at ambient temperature during 16 h. The mixture was extracted from 0.1M NaOH into DCM, dried on Na2SO4, concentrated, and chromatographed on silica gel (0→2% EtOAc/hexanes) to give 6-phenoxynaphthalene-2-boronic acid pinacol ester, which was deprotected via Method 5 to provide compound 216 (54 mg, 37%). [M−H]−=263.1 m/z. Activity: A

Workup

  1. extractionThe mixture was extracted from 0.1M NaOH into DCM
  2. customdried on Na2SO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (0→2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ee39f41c15d344dcb8537e5f791f5afb
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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