Sodium hydride → HCID 59314412, compound

HRID 1047905Notes

Reaction equation

HRID 1047905 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[OH:28])=[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].[H-].[Na+].[CH:31]1(Br)[CH2:34][CH2:33][CH2:32]1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[O:28][CH:31]2[CH2:34][CH2:33][CH2:32]2)=[O:17])[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 24758Sodium hydrideHCID 78110BromocyclobutaneHCID 59314204HCID 59314204, compound

Product 1

HCID 59314412HCID 59314412, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(1-hydroxynaphthalene-2-carbonyl)amino]indan-2-carboxylic acid ethyl ester (289) (560 mg, 1.5 mmol) in dry DMF is treated with NaH oil dispersion (60%, 100 mg, 2.25 mmol, 1.5 eq) and stirred for 10 min. The cyclobutyl bromide (405 mg, 3 mmol, 2 eq) is added and the reaction heated and stirred in the microwave at 150° C. for 3 hours. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (75 mL) and washed with water (2×30 mL) and brine (30 mL). The organic layer is dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (200 g silica gel, 10% EtOAc in heptane) to give white solid. (290 mg, 45%)

Workup

  1. temperaturethe reaction heated
  2. stirringstirred in the microwave at 150° C. for 3 hours
  3. customAfter the removal of DMF in vacuo
  4. dissolutionthe residue is dissolved in EtOAc (75 mL)
  5. washwashed with water (2×30 mL) and brine (30 mL)
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography (200 g silica gel, 10% EtOAc in heptane)
  9. customto give white solid

Sources & evidence

ORD record
ord-1b121f35a4cd4410a9f01298948d911c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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