Ethyl Acetate → (2-(4-Methylthiazol-2-ylamino)pyridin-4-yl)(phenyl)methanol

HRID 911002Notes

Reaction equation

HRID 911002 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1[N:11]=[C:12]([NH:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][N:23]=2)[CH:19]=[O:20])[S:13][CH:14]=1.C(OCC)(=O)C>CCOCC.C1COCC1>[CH3:9][C:10]1[N:11]=[C:12]([NH:15][C:16]2[CH:17]=[C:18]([CH:19]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[OH:20])[CH:21]=[CH:22][N:23]=2)[S:13][CH:14]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 86634740HCID 86634740, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 24826745(2-(4-Methylthiazol-2-ylamino)pyridin-4-yl)(phenyl)methanolYield 40.05%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 M Phenylmagnesium bromide (0.9982 mL, 2.995 mmol) in ether was added to THF (2 mL) at 0° C., and then 2-(4-methylthiazol-2-ylamino)isonicotinaldehyde (0.197 g, 0.8985 mmol) in THF (3 mL) was added. The reaction mixture was stirred for 30 minutes, then partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was washed with brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 2:3 hexane:ethyl acetate to afford (2-(4-methylthiazol-2-ylamino)pyridin-4-yl)(phenyl)methanol (0.107 g, 40.05% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.10 (s, 1H), 8.14 (d, 1H), 7.24-7.37 (m, 5H), 7.11 (s, 1H), 6.81 (d, 1H), 6.50 (s, 1H), 6.09 (d, 1H), 5.64 (d, 1H), 2.22 (s, 3H).

Workup

  1. custompartitioned between saturated ammonium chloride and ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with 2:3 hexane

Sources & evidence

ORD record
ord-78955d4c1c9840af8bf9951a6c63386a
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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