Diisopropylethylamine → HCID 86721072, compound

HRID 930931Notes

Reaction equation

HRID 930931 reaction equation
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.C(N(C(C)C)C(C)C)C.[Br:17][C:18]1[CH:19]=[C:20]([S:25](Cl)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[F:24]>ClCCl>[Br:17][C:18]1[CH:19]=[C:20]([S:25]([N:5]2[CH2:6][C:3]([F:7])([F:2])[CH2:4]2)(=[O:26])=[O:27])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 86721072HCID 86721072, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3,3-difluoroazetidine hydrochloric acid (0.947 g, 7.31 mmol) in 20 mL dichloromethane at 0° C. was added N-ethyl-N-isopropylpropan-2-amine (2.80 mL, 16.1 mmol) followed by the addition of a solution of 3-bromo-4-fluorobenzene-1-sulfonyl chloride (2.0 g, 7.3 mmol) in 4 mL dichloromethane. The mixture was stirred at room temperature overnight and then heated at 55° C. for 5 hours, diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by flash chromatography (silica gel, 10-50% ethyl acetate/heptanes gradient) to give the title compound (1.5 g, 62.1% yield)

Workup

  1. temperatureheated at 55° C. for 5 hours
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography (silica gel, 10-50% ethyl acetate/heptanes gradient)

Sources & evidence

ORD record
ord-feade8799ed647a2b9edb11254f71dc9
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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