Toluene → HCID 89525658, compound

HRID 2278356Notes

Reaction equation

HRID 2278356 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[S:5][CH:6]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC=CC=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([N:17]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:12])[CH3:11])[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 7369Benzenesulfonyl chlorideHCID 131733452HCID 131733452, compound

Product 1

HCID 89525658HCID 89525658, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

N-[1-(4-bromothiophen-2-yl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-3-methylbutan-1-amine (248 mg, 0.610 mmol) and DMAP (3.7 mg, 0.031 mmol) were dissolved in 2 mL pyridine and benzenesulfonyl chloride (234 μl, 1.830 mmol) was added. The resulting mixture was heated at 75° C. overnight, after which the mixture was cooled to room temperature, toluene was added and the mixture was concentrated in vacuo. The title compound was purified on silica gel (EtOAc/hexanes).

Workup

  1. temperatureafter which the mixture was cooled to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe title compound was purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-2e9911b77dd445de9b0168c45f3d45ce
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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