Methanol → HCID 11324268, compound

HRID 1592965Notes

Reaction equation

HRID 1592965 reaction equation
[C:1]1([C:7]2([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=4)[C:18]#N)[N:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:24]>[Zn]>[C:1]1([C:7]2([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]([CH2:18][OH:24])[CH:20]=[CH:21][CH:22]=4)[N:14]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 11335659HCID 11335659, compound

Product 1

HCID 11324268HCID 11324268, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]benzonitrile (1-10, 0.10 g, 0.33 mmol) in MeOH (20 mL) was treated with NiCl2-6H2O (0.24 g, 1.0 mmol) and Zn metal (0.17 g, 2.6 mmol) and the resulting mixture was stirred vigorously at reflux for 72 h. The reaction was filtered through celite, concentrated, and partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was concentrated and the crude residue was purified by reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA) to provide pure {3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]phenyl}methanol (5-1): 1H NMR (300 MHz, CDCl3) δ 7.82 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.52 (dt, J=6.8, 1.3 Hz, 2H), 7.40-7.30 (m, 5H), 7.32 (s, 1H), 4.76 (s, 2H), 1.87 (dd, J=6.8, 3.9 Hz, 2H), 1.44 (dd, J=6.8, 3.9 Hz, 2H); MS 307.9 found 309.4 (M+H+) required.

Workup

  1. temperatureat reflux for 72 h
  2. filtrationThe reaction was filtered through celite,
  3. concentrationconcentrated
  4. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
  5. concentrationThe organic layer was concentrated
  6. customthe crude residue was purified by reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA)

Sources & evidence

ORD record
ord-cbe083a35aa04f1694f742b40bf5f2e4
Source dataset
uspto-grants-2007_11
Patent number
US07294640B2

Reaction notes

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