HCID 86680497, compound → HCID 71544070, compound

HRID 2406490Notes

Reaction equation

HRID 2406490 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[O:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[CH:21]([Mg]Br)([CH3:23])[CH3:22]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:13]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)([OH:14])[CH:21]([CH3:23])[CH3:22])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86680497HCID 86680497, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 71544070HCID 71544070, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-(4-fluorophenyl)thiazol-5-yl)(pyridin-4-yl)methanone (0.1 g, 0.352 mmol) in THF (10 mL) was added isopropyl magnesium bromide (0.1 g, 0.704 mmol) at 0° C. The reaction mixture was stirred for 1 hour at room temperature. After completion of the reaction, the reaction mixture was quenched with ammonium chloride (5 mL) at 0° C., extracted with ethyl acetate (2×20 mL), washed with water followed by brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude was purifying by the preparative TLC (Mobile phase: 10% MeOH in DCM) to obtain pure 1-(2-(4-fluorophenyl)thiazol-5-yl)-2-methyl-1-(pyridin-4-yl)propan-1-ol (0.023 g, 20% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (d, 2H), 7.92 (t, 3H), 7.56 (d, 2H), 7.27 (t, 2H), 6.22 (s, 1H), 2.79 (t, 1H), 0.98 (d, 3H), 0.71 (d, 3H); LC-MS m/z calculated for [M+H]+ 329.10, found 329.1.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with ammonium chloride (5 mL) at 0° C.
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purifying by the preparative TLC (Mobile phase: 10% MeOH in DCM)

Sources & evidence

ORD record
ord-11542c9fffe24fbfb6e9ae2297d399d2
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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