Diisopropylamine → HCID 66699464, compound
Reaction equation
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]#[N:20].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]=[O:30])=[C:24]([Cl:31])[CH:23]=1.CC(C1C=CC(Br)=CC=1Cl)=O>C1COCC1.O>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:1])[CH:29]([C:17]2[S:16][C:15]([C:19]#[N:20])=[C:14]([CH3:13])[CH:18]=2)[OH:30])=[C:24]([Cl:31])[CH:23]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-butyllithium (1.6M) in hexanes (0.18 ml) was added to a solution of diisopropylamine (0.212 ml) in THF (2 ml) at 0° C. The mixture was stirred for 5 min and then cooled to −78° C. 3-Methylthiophene-2-carbonitrile (184 mg, CAS Reg. No. 55406-13-8) was added at −78° C. and then stirred for 30 min. A solution of 2-(4-bromo-2-chlorophenyl)ethanone (248 mg, CAS Reg. No. 749932-89-6, prepared in analogy to Example 58, step 2, from 2-chloro-4-bromoacetophenone [CAS Reg. No. 252561-81-2]) in THF (1 ml) was added at −78° C. The mixture was stirred for 20 min, then water (0.2 ml) was added. The mixture was filtered over celite and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (100 mg) as a colorless oil. MS (m/e)=370.0 [M+H+].
Workup
- addition55406-13-8) was added at −78° C.
- stirringstirred for 30 min
- stirringThe mixture was stirred for 20 min
- filtrationThe mixture was filtered over celite
- concentrationconcentrated to an oil
- customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)
Sources & evidence
- ORD record
- ord-17615b22984a4cfc84b1a85c614357de
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138189B2
Reaction notes
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