Hexane → 1-dibutylcarbamoyl-1H-indole-4-carboxylic acid

HRID 1261089Notes

Reaction equation

HRID 1261089 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.CCCCCC.[CH2:24]([N:28]([CH2:32][CH2:33][CH2:34][CH3:35])[C:29](Cl)=[O:30])[CH2:25][CH2:26][CH3:27]>O1CCCC1>[CH2:24]([N:28]([CH2:32][CH2:33][CH2:34][CH3:35])[C:29]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1)=[O:30])[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 8058HexaneHCID 83371Dibutylcarbamoyl chlorideHCID 595229Indole-4-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 666792741-dibutylcarbamoyl-1H-indole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1H-Indole-4-carboxylic acid (611, 251 mg, 1.56 mmol) in tetrahydrofuran (3 mL), was added 2.5M n-butyllithium in hexane (1.28 mL, 3.19 mmol) at −78° C. After 30 minutes, dibutyl carbamyl chloride (657 mg, 3.43 mmol) was added and stirred for two hours. The reaction solution was quenched with 1M HCl (aq.) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated and concentrated. The desired compound was isolated with silica gel column chromatography using 10% ethyl acetate in hexane to give a white solid (612, 88 mg, 18%). MS (ESI) [M−H+]−=315.1.

Workup

  1. customThe reaction solution was quenched with 1M HCl (aq.)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-383cbfe3ddb543f28432843d96372158
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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