2-Bromopropane → 2-(3,5-Dichloro-2-isopropoxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047688Notes

Reaction equation

HRID 1047688 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][S:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[C:20]=2[OH:27])(=[O:18])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:35]([CH3:37])[CH3:36]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][S:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[C:20]=2[O:27][CH:35]([CH3:37])[CH3:36])(=[O:18])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 593143742-(3,5-Dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143602-(3,5-Dichloro-2-isopropoxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(3,5-dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester (30) (226 mg, 0.53 mmol), anhydrous Cs2CO3 (300 mg, 0.92 mmol), and KI (15 mg, 0.09 mmol) in DMF (15 mL) is added 2-bromopropane (432, 4.60 mmol). The resulting reaction suspension is filled with argon and run in a microwave reaction: 110° C., 2.5 h. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 10%-60% EtOAc in heptane) to give a pure product (31) as a white semi-solid (248 mg, 100%).

Workup

  1. customThe resulting reaction suspension
  2. additionis filled with argon
  3. customrun in a microwave reaction
  4. custom110° C., 2.5 h
  5. customAfter the removal of DMF in vacuo
  6. dissolutionthe residue is dissolved in EtOAc (30 mL)
  7. washwashed with water (1×5 mL) and brine (2×5 mL)
  8. dry with materialThe organic layer is dried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 10%-60% EtOAc in heptane)

Sources & evidence

ORD record
ord-ab7fbcec8fd04aa48df218fc98ae0f98
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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