Ammonium Chloride → HCID 58019885, compound

HRID 1632047Notes

Reaction equation

HRID 1632047 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[O:16][CH:17]=[N:18][N:19]=3)[CH:10]=2)=[CH:7][C:6]([CH:20]=[O:21])=[CH:5][CH:4]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1.[NH4+].[Cl-]>C1COCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:20]([C:6]2[CH:7]=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4[O:16][CH:17]=[N:18][N:19]=4)[CH:10]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[OH:21])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86637552HCID 86637552, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 58019885HCID 58019885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the above aldehyde, 6-Methoxy-3′-[1,3,4]oxadiazol-2-yl-biphenyl3-carbaldehyde (86 mg, 0.307 mmol) in anhydrous THF (1 mL) was added dropwise a solution of 4-fluorophenyl magnesium bromide in THF (0.46 ml, 1M) at −78° C. After the addition was complete, the resulting mixture was allowed to warm to room temperature and stirred for 40 minutes. Then saturated NH4Cl aq. was added. The mixture was extracted with EtOAc (2×10 ml). The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent gave a residue, which was purified by chromatography on silica gel to give 112 mg of the product (P-117). 1H NMR (400 MHz, CDCl3) δ ppm 3.82 (s, 3H), 5.85 (s, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.98-7.05 (m, 2H), 7.31-7.39 (m, 4H), 7.54 (t, 1H), 7.67-7.7 (m, 1H), 8.01-8.04 (m, 1H), 8.23 (s, 1H), 8.46 (s, 1H) ppm; LCMS (ESI+): 377 (M+1).

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with EtOAc (2×10 ml)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. customRemoval of solvent
  6. customgave a residue, which
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a5c680047a694bbcbf411423d5af8ae5
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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