Potassium Carbonate → HCID 86718782, compound

HRID 929601Notes

Reaction equation

HRID 929601 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.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.O>[C:11]([NH:8][CH2:7][C:6]1[CH:15]=[C:2]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)[CH:3]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]=1[OH:10])([CH3:12])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 86718776HCID 86718776, compound

Product 1

HCID 86718782HCID 86718782, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
60.5 °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) (0.485 g, 1.41 mmol), pyridin-3-ylboronic acid (0.346 g, 2.0 equiv), and potassium carbonate (0.777 g, 4 equiv) in isopropanol (30 mL) and water (6 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)Pd (0) (90 mg, 5.5 mol %) was added and the resulting mixture was heated at 55-66° C. for 3 hours. The cooled reaction mixture was concentrated and the resulting residue was purified by column chromatograph to give 3-((tert-butylamino)methyl)-5-(pyridine-3-yl)-[1,1′-biphenyl]-2-ol (0.233 g).

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. additionTetrakis(triphenylphosphine)Pd (0) (90 mg, 5.5 mol %) was added
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated
  5. customthe resulting residue was purified by column chromatograph

Sources & evidence

ORD record
ord-f4ef4916570447eab8f4e9e9dbb0b63b
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

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