Methanesulfonyl chloride → HCID 90103173, compound

HRID 1052619Notes

Reaction equation

HRID 1052619 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[C:5]([NH2:18])[CH:4]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:19][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([NH:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH:6]=[C:7]([B:9]2[O:10][C:11]([CH3:17])([CH3:16])[C:12]([CH3:14])([CH3:15])[O:13]2)[CH:8]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131074365N1,N1-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine

Product 1

HCID 90103173HCID 90103173, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

N1,N1-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine (324 mg, 1.24 mol) was dissolved in 11 mL pyridine. The mixture was submitted to three vacuum-argon cycles and was cooled at 0° C. with an ice bath. Methanesulfonyl chloride (110 μl, 1.42 mol) was added dropwise and the reaction mixture was stirred overnight. The solvent was concentrated and the residue was partitioned between dichloromethane and a saturated sodium bicarbonate solution. The organic phase was dried over sodium sulphate and evaporated under reduced pressure. The semi-solid was crystallized in hexane to obtain a solid that was filtered off and dried in the oven to give 365 mg (87% yield) of the final compound as a mixture of boronic acid and boronate ester. Purity 100%.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe semi-solid was crystallized in hexane
  6. customto obtain a solid
  7. filtrationthat was filtered off
  8. customdried in the oven

Sources & evidence

ORD record
ord-813c43590471438b8deb6b3ca47076b8
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…