Potassium Carbonate → HCID 86718775, compound

HRID 929597Notes

Reaction equation

HRID 929597 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[O:10]C[N:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][C:6]=2[CH:15]=1.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[C:23]1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOCCOC.O.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>[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH:24]=[C:23]1[C:2]1[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]([OH:10])=[C:6]([CH2:7][NH:8][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acid2×HCID 86718776HCID 86718776, compound

Product 1

HCID 86718775HCID 86718775, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8150DiglymeSolvent

Conditions

Temperature
56.5 °C

Procedure

A mixture of 6-bromo-3-(tert-butyl)-8-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazine (from Example 42, Step 2) (0.552 g, 1.6 mmol), benzofuran-2-ylboronic acid (0.387 g, 1.5 equiv), and potassium carbonate (0.885 g, 4 equiv) in 2-methoxyethyl ether (10 mL) and water (2 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)Pd (0) (82 mg, 0.073 mmol, 4.5 mol %) was added and the resulting mixture was heated at 51-62° C. for 1.5 hours. To the reaction mixture, additional benzofuran-2-ylboronic acid (0.173 g, 1.07 mmol) was added. The resulting mixture was allowed to heat at 60-62° C. overnight. The cooled reaction mixture was concentrated and the resulting residue was purified by column chromatography to give 5-(benzofuran-2-yl)-3-((tert-butylamino)methyl)-[1,1′-biphenyl]-2-ol (0.315 g).

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. temperatureto heat at 60-62° C. overnight
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-fad0263e710a4c66855f420615e10ed1
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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