Diisopropylethylamine → 4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)thiomorpholine 1,1-dioxide

HRID 1049665Notes

Reaction equation

HRID 1049665 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[NH:27]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]1>C(Cl)Cl.CO>[CH3:16][C:11]1([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13][B:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:27]3[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]3)=[CH:4][CH:5]=2)[O:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 593927824-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1 eq) and DIPEA (2 eq) are dissolved in DCM/MeOH (5:1 v:v) under N2 and thiomorpholine 1,1-dioxide (2 eq) is added portionwise. The resulting solution is stirred at room temperature for 16 h. After this time, the reaction is complete. The solvent is evaporated. The compound is extracted with EtOAc and water, washed with brine and dried over anhydrous MgSO4. Organic layers are filtered and evaporated. The final compound is isolated without further purification.

Workup

  1. customThe solvent is evaporated
  2. extractionThe compound is extracted with EtOAc and water
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationOrganic layers are filtered
  6. customevaporated

Sources & evidence

ORD record
ord-d43c5a0977484d10aa6ae0d484fea1ae
Source dataset
uspto-grants-2016_07
Patent number
US09382247B2

Reaction notes

Loading…