2-Naphthol → HCID 68508122, compound

HRID 876359Notes

Reaction equation

HRID 876359 reaction equation
C[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.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1O>C1COCC1.ClCCl>[CH:28]1[C:29]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:27]=1[O:9][CH:6]1[CH2:7][CH2:8][NH:2][CH2:3][C:4]2[CH:13]=[C:12]([C:14]3[N:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=[CH:10][C:5]1=2

Participants

5

Reactant 2

HCID 86632-NaphtholHCID 68502906HCID 68502906, compound

Product 1

HCID 68508122HCID 68508122, compoundYield 52.1%

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 (80 mg, 0.31) from Step H above in THF (5 mL) was added napthalen-2-ol (67 mg, 0.47 mmol), tributylphosophine (95 mg, 0.47 mmol) and 1,1′-(azodicarboyl)dipiperidine (118 mg, 0.47 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 the (+)-5-(naphthalen-2-yloxy)-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine (60 mg, 48%) 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-468da5b856f945b2aa59560e22cf0fdd
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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