Phenol → HCID 25156308, compound

HRID 876363Notes

Reaction equation

HRID 876363 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH:6]([OH:9])[C:5]2[CH:10]=[CH:11][C:12]([C:14]3[N:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][C:4]=2[CH2:3]1.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.ClCCl>[CH3:1][N:2]1[CH2:8][CH2:7][CH:6]([O:9][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[CH:10]=[CH:11][C:12]([C:14]3[N:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][C:4]=2[CH2:3]1

Participants

5

Reactant 2

HCID 996PhenolHCID 68502906HCID 68502906, compound

Product 1

HCID 25156308HCID 25156308, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (+)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-ol (65 mg, 0.25) from Step A in THF (5 mL) was added phenol (73 mg, 0.77 mmol), tributylphosophine (156 mg, 0.77 mmol) and 1,1′-(azodicarboyl)dipiperidine (192 mg, 0.77 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with dichloromethane and washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography (98:2 to 95:5 ethyl acetate/methanol), followed by HPLC to give (−)-2-methyl-5-phenoxy-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine (52 mg, 62%) as a gum-like solid.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (98:2 to 95:5 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-7dcd5e8a6e534b8c98d79a9d0765d050
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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