Dimethylformamide → HCID 89525690, compound

HRID 2278357Notes

Reaction equation

HRID 2278357 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]([N:17]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[S:5][CH:6]=1.[Li]CCCC.CN([CH:40]=[O:41])C>C1COCC1>[Si:10]([O:9][CH2:8][CH:7]([N:17]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:4]1[S:5][CH:6]=[C:2]([CH:40]=[O:41])[CH:3]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 89525658HCID 89525658, compoundHCID 178418339Butyllithium

Product 1

HCID 89525690HCID 89525690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[1-(4-bromothiophen-2-yl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-N-(3-methylbutyl)benzenesulfonamide (227 mg, 0.415 mmol) was dissolved in 4.1 mL THF and cooled to −78° C. n-BuLi (174 μl (2.5M in hexanes), 0.436 mmol) was added dropwise. The mixture was stirred 5 minutes and DMF (322 μL) was added in one portion. The mixture was stirred 20 minutes and then quenched with aqueous ammonium chloride. The quenched mixture was warmed to room temperature, DCM was added and the phases separated with a phase extractor. The solvent was removed under reduced pressure. The title compound was purified on silica gel (EtOAc/hexanes).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred 20 minutes
  3. customquenched with aqueous ammonium chloride
  4. additionDCM was added
  5. customthe phases separated with a phase extractor
  6. customThe solvent was removed under reduced pressure
  7. customThe title compound was purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2b16b87544544e85a20e2c12326c3409
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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