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

HRID 925497Notes

Reaction equation

HRID 925497 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) were dissolved in DCM/MeOH (5:1 v:v) under N2 and thiomorpholine 1,1-dioxide (2 eq) was added portion wise. The resulting solution was stirred at room temperature for 16 h. After this time, the reaction was complete. The solvent was evaporated. The compound was extracted with EtOAc and water, washed with brine and dried over anhydrous MgSO4. Organic layers were filtered and evaporated. The final compound was isolated without further purification.

Workup

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

Sources & evidence

ORD record
ord-af5e63a8740541cb8aaf8f20369de7d9
Source dataset
uspto-grants-2016_03
Patent number
US09284311B2

Reaction notes

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