2-Bromopropane → HCID 59314329, compound

HRID 1047682Notes

Reaction equation

HRID 1047682 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([O-])([O-])=O.[Cs+].[Cs+].Br[CH:36]([CH3:38])[CH3:37]>CN(C=O)C>[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[O:27][CH:36]([CH3:38])[CH3:37])[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]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 59314109HCID 59314109, compound

Product 1

HCID 59314329HCID 59314329, compoundYield 73%

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 (16 mg, 0.09 mmol) in DMF (8 mL) is added 2-bromo-propane (220 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 the pure product (25) as white solid (143 mg, 73%).

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-bfaacfa0b9844e7ead0b88241078e07e
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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