Diethyl Ether → HCID 86638344, compound

HRID 2390850Notes

Reaction equation

HRID 2390850 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([C:11]#N)[CH3:10])[CH:7]=1.CC(C[AlH]CC(C)C)C.CC[O:41]CC>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([CH:11]=[O:41])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydride2×HCID 67070089HCID 67070089, compound

Product 1

HCID 86638344HCID 86638344, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 288 (766 mg, 1.599 mmol) in DCM (10 mL) at 0° C. was added DIBAL (3.2 mL, 3.2 mmol, 1.0M in DCM). The reaction mixture was gradually warmed to RT overnight. LCMS indicated incomplete conversion. Additional DIBAL (3.2 mL, 3.2 mmol) was added and the reaction mixture was stirred for an additional 5 h. The reaction mixture was cooled to 0° C. and diluted with ether (20 mL). The reaction was quenched by careful addition of 6N HCl (1.5 mL). The resulting suspension was extracted with EtOAc and the organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatograph eluting with an EtOAc/hexane gradient (20% to 30% EtOAc) to afford 263 mg (34%) of N-{4-[2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-1-formyl-1-methyl-ethyl]-phenyl}-methanesulfonamide (292) as a tan oil.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe reaction was quenched by careful addition of 6N HCl (1.5 mL)
  3. extractionThe resulting suspension was extracted with EtOAc
  4. dry with materialthe organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by SiO2 chromatograph
  8. washeluting with an EtOAc/hexane gradient (20% to 30% EtOAc)

Sources & evidence

ORD record
ord-f4871197b3d64cb8955c109616680c63
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

Loading…