Ammonium Chloride → HCID 25008471, compound

HRID 607095Notes

Reaction equation

HRID 607095 reaction equation
[CH3:1][Mg+].[Br-].[F:4][C:5]([F:51])([F:50])[C:6]1[CH:7]=[C:8]([C@H:16]2[O:20][C:19](=[O:21])[N:18]([CH2:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=3[C:33]3[CH:34]=[C:35]([C:40]4[CH:45]=[CH:44][C:43]([CH:46]=[O:47])=[CH:42][C:41]=4[CH3:48])[CH:36]=[CH:37][C:38]=3[Cl:39])[C@H:17]2[CH3:49])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1.[Cl-].[NH4+]>C1COCC1>[F:51][C:5]([F:4])([F:50])[C:6]1[CH:7]=[C:8]([C@H:16]2[O:20][C:19](=[O:21])[N:18]([CH2:22][C:23]3[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=[CH:25][C:24]=3[C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[C:35]([C:40]4[CH:45]=[CH:44][C:43]([CH:46]([OH:47])[CH3:1])=[CH:42][C:41]=4[CH3:48])[CH:34]=3)[C@H:17]2[CH3:49])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 25008472HCID 25008472, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 25008471HCID 25008471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

MeMgBr (0.274 ml, 0.274 mmol, 1 M solution) was added to a solution of aldehyde from Example 50 (160 mg, 0.229 mmol) in THF (3 ml) at −78° C. The solution was stirred at −78° C. for 2 h. Saturated ammonium chloride solution was added. The mixture was extracted with EtOAc (3×10 ml). The combined EtOAc layers were washed with brine, and dried over sodium sulfate. The residue was purified by flash column on silica gel, eluting with EtOAc/hexane (30:70) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz): δ a mixture of 1:1 atopoisomers 7.89 (s, 1H), 7.72 (m, 4H), 7.58 (d, J=8.5 Hz, 1H), 7.48 (m, 1H), 7.38 (m, 1H), 7.32-7.20 (m, 4H), 5.62 (d, J=8.0 Hz, 1H), 5.00 (d, J=15.5 Hz, 0.5H), 4.93 (m, 1H), 4.82 (d, J=16.0 Hz, 0.5H), 4.10 (d, J=15.5 Hz, 0.5H), 4.01 (d, J=15.5 Hz, 0.5H), 3.88 (m, 0.5H), 3.87 (m, 0.5H), 2.34 (s, 1.5H), 2.33 (s, 1.5H), 1.55 (m, 3H), 0.61 (d, J=6.5 Hz, 1.5H), 0.58 (d, J=6.5 Hz, 1.5H). LC/MS: M+−18: 698.16.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×10 ml)
  2. washThe combined EtOAc layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe residue was purified by flash column on silica gel
  5. washeluting with EtOAc/hexane (30:70)

Sources & evidence

ORD record
ord-fd4c5c859b42488a882a94980e93f2e2
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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