Dimethylformamide → 5-[1-(4-Chloro-3-methyl-phenyl)-propylamino]-2-methyl-benzaldehyde

HRID 1629705Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[CH:14]=2)[CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].[Li]C(C)(C)C.CN([CH:29]=[O:30])C>CCOCC>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH:3]=2)[CH:29]=[O:30])[CH2:11][CH3:12])=[CH:14][C:15]=1[CH3:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of INT 8 (2.20 g, 14.7 mmol) in Et2O (147 mL) at −78° C. was added tBuLi (1.7 M in pentane, 34.7 mL, 59.0 mmol) dropwise. The mixture was stirred at −78° C. for 40 min, then DMF (2.5 mL) was added. The reaction mixture was stirred at −78° C. for an additional 20 minutes. The mixture was quenched with saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane/EtOAc) to afford INT 9.

Workup

stirringThe reaction mixture was stirred at −78° C. for an additional 20 minutes
customThe mixture was quenched with saturated aqueous NH4Cl
extractionextracted with Et2O (2×)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (heptane/EtOAc)
customto afford INT 9

Sources & evidence

ORD record: ord-41faebf0d571430cb2663253f59bc144
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791100B2

Reaction notes

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