Ammonium Chloride → HCID 71184068, compound

HRID 1519228Notes

Reaction equation

HRID 1519228 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH:21]=[O:22])=[N:6][CH:7]=1.[CH3:23][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH:21]([OH:22])[CH3:23])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86675604HCID 86675604, compound2×HCID 178418573HCID 178418573, compound

Product 1

HCID 71184068HCID 71184068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carbaldehyde (intermediate B4.1, 0.05 g, 0.15 mmol) in THF (1.3 ml) was added 3M methylmagnesium bromide (0.06 ml, 0.18 mmol) at 0° C. The reaction was allowed to warm to rt and satd. aq. NH4Cl was added. Extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, concentrated and purified by flash chromatography (silica, 20-50% EtOAc/hexanes) to give 1-{5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}ethanol. 1H NMR (400 MHz, CDCl3) δ 8.36 (d, 2.5 Hz, 1H), 8.06 (m, 2H), 7.52 (dd, J=8.4, 2.5 Hz, 1H), 7.12 (m, 3H), 5.02 (m, 1H), 3.22 (d, J=5.2 Hz, 1H), 1.56 (m, 3H); LCMS [M+H]+=351.3.

Workup

  1. extractionExtracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica, 20-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a15ea449004f460fab4f6f435494095b
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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