Water → HCID 57975345, compound

HRID 1865055Notes

Reaction equation

HRID 1865055 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12][C:13]1([CH3:29])[C:17]([CH3:19])([CH3:18])[O:16][B:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH2:28])=[CH:22][CH:21]=2)[O:14]1.[CH:30]([S:33](Cl)(=[O:35])=[O:34])([CH3:32])[CH3:31].O>ClCCl>[CH3:19][C:17]1([CH3:18])[C:13]([CH3:29])([CH3:12])[O:14][B:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH:28][S:33]([CH:30]([CH3:32])[CH3:31])(=[O:35])=[O:34])=[CH:22][CH:21]=2)[O:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 68522131HCID 68522131, compound

Product 1

HCID 57975345HCID 57975345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add DBU (0.79 mL, 5.3 mmol) to 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylamine (0.5 g, 1.8 mmol, can be prepared from 4-bromophenyl acetonitrile) in dichloromethane and stir at room temperature. After 10 minutes, cool to 0° C. and add isopropylsulfonylchloride (0.22 mL, 1.95 mmol). After 30 minutes, allow to warm to room temperature. After 3 hours, pour into water and extract with dichloromethane. Wash the combined organics with 1N HCl, water, and brine, dry over magnesium sulfate, filter and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (ES−)=352.2 (M−1).

Workup

  1. temperaturecool to 0° C.
  2. waitAfter 30 minutes
  3. temperatureto warm to room temperature
  4. waitAfter 3 hours
  5. extractionextract with dichloromethane
  6. washWash the combined organics with 1N HCl, water, and brine
  7. dry with materialdry over magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure
  10. customPurify the residue by flash chromatography (silica gel)
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-b15b6d8139704939a3b887f340ff3fac
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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