Cerium(III) chloride → HCID 178459058, compound

HRID 253631Notes

Reaction equation

HRID 253631 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:19])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=2[F:32])/[S:10]1)([CH3:8])([CH3:7])[CH3:6].[CH3:34][Mg]Br>C1COCC1>[C:5]([N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])([CH3:34])[CH3:18])/[C:11](=[N:20]/[C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[C:23]=2[F:32])/[S:10]1)([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 178418573HCID 178418573, compoundHCID 178467761HCID 178467761, compound

Product 1

HCID 178459058HCID 178459058, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of cerium(III) chloride (86 mg, 0.35 mmol) in THF (3 mL) was added the product from Example 77 (100 mg, 0.23 mmol) in THF (0.5 mL). The mixture was stirred at rt for 1 hr. The above mixture was cooled to −40° C. and methylmagnesium bromide (41.6 mg, 0.348 mmol) was added dropwise. The reaction was stirred for 40 min at −40° C., quenched with saturated aqueous NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 57 mg (55%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.23 (s, 6H) 1.57-1.61 (m, 2H) 1.68 (s, 9H) 1.74 (s, 1H) 1.81-1.89 (m, 2H) 2.88 (t, J=7.63 Hz, 2H) 7.30 (t, J=7.93 Hz, 1H) 7.69 (t, J=6.41 Hz, 1H) 8.01-8.04 (m, 1H) 8.39 (td, J=7.93, 1.53 Hz, 1H); MS (DCI/NH4+) m/z 447 (M+H)+.

Workup

  1. temperatureThe above mixture was cooled to −40° C.
  2. stirringThe reaction was stirred for 40 min at −40° C.
  3. customquenched with saturated aqueous NH4Cl
  4. extractionextracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-24be895d4a774701ab0c6c63a8abb345
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Reaction notes

Loading…