Allyl bromide → 2-(2-Allyloxy-3-chloro-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047674Notes

Reaction equation

HRID 1047674 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[OH:24])[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[CH2:33][CH:34]=[CH2:35]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[O:24][CH2:35][CH:34]=[CH2:33])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 593141222-(3-Chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593142682-(2-Allyloxy-3-chloro-benzoylamino)-indan-2-carboxylic acid ethyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(3-chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester (14) (250 mg, 0.69 mmol), anhydrous Cs2CO3 (453 mg, 1.39 mmol), and KI (23 mg, 0.14 mmol) in DMF (10 mL) is added 3-bromo-propene (70 μL, 0.83 mmol). The resulting reaction suspension is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (20 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 (80 g silica gel, gradient elution: 10-40% EtOAc in heptane) to give a pure product (17) as white solid (160 mg, 58%).

Workup

  1. customThe resulting reaction suspension
  2. customAfter the removal of DMF in vacuo
  3. dissolutionthe residue is dissolved in EtOAc (20 mL)
  4. washwashed with water (1×5 mL) and brine (2×5 mL)
  5. dry with materialThe organic layer is dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash column chromatography (80 g silica gel, gradient elution: 10-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-acfbf89732674dd9b1b54ac1895b9804
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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