Sodium hydride → HCID 86659856, compound

HRID 2360116Notes

Reaction equation

HRID 2360116 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[H-].[Na+].[CH:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1)([CH3:16])[CH3:15]>C(OCC)C>[CH:14]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:25])[O:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:19][CH:18]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 94416p-Isopropylphenyl isocyanateHCID 21029540HCID 21029540, compound

Product 1

HCID 86659856HCID 86659856, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-methylindolin-5-ol (18 mg, 0.12 mmol) in 0.6 mL of dry diethyl ether was added sodium hydride (55%, 19 mg, 0.43 mmol) at room temperature. After the reaction mixture was stirred at the same temperature for 2 min, 4-isopropylphenylisocyanate (29 μL, 0.18 mmol) was added with additional stirring for 5 min to 10 min. After the reaction mixture was quenched with water (1 mL), the solution was extracted with diethyl ether (10 mL). The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 60/40) to obtain the title compound (5.4 mg, 14%).

Workup

  1. stirringwith additional stirring for 5 min to 10 min
  2. customAfter the reaction mixture was quenched with water (1 mL)
  3. extractionthe solution was extracted with diethyl ether (10 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 60/40)

Sources & evidence

ORD record
ord-0627b78d89dd4aef83d5971eb607fb8a
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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