Allyl bromide → HCID 68590795, compound

HRID 1047680Notes

Reaction equation

HRID 1047680 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=2[OH:27])[CH2:16][C:15]2[C:17]3[C:11]([CH:12]=[CH:13][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:6]1)=[O:4].[C:29]([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][CH:37]=[CH2:38]>CN(C=O)C>[CH2:1]([O:2][C:3]([C:5]1([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=2[O:27][CH2:36][CH:37]=[CH2:38])[CH2:6][C:7]2[C:17]3[C:11]([CH:10]=[CH:9][CH:8]=2)=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16]1)=[O:4])[CH3:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 59314109HCID 59314109, compound

Product 1

HCID 68590795HCID 68590795, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(2-hydroxy-3-methyl-benzoylamino)-2,3-dihydro-1H-phenalene-2-carboxylic acid methyl ester (22) (175 mg, 0.47 mmol), anhydrous Cs2CO3 (306 mg, 0.94 mmol), and KI (15.6 mg, 0.09 mmol) in DMF (8 mL) is added 3-bromo-propene (199 μL, 2.35 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 (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane) to give a pure product (23) as white solid (107 mg, 55%).

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 (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-4373314c62a04d0282d0bddb8e3db91d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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