Sodium hydride → HCID 60161544, compound

HRID 1843295Notes

Reaction equation

HRID 1843295 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]=[C:23]=[O:24]>CN(C)C=O>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:24])[O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH2:5][CH2:4][CH2:3][N:2]2[CH3:1])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 855882-Fluorophenyl isocyanateHCID 137509151-Methyl-1,2,3,4-tetrahydroquinolin-7-ol

Product 1

HCID 60161544HCID 60161544, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-methyl-1,2,3,4-tetrahydroquinolin-7-ol (500 mg, 2.09 mM) in dry dimethylformamide (DMF, 5 mL) was added to the stirred solution of sodium hydride in dry DMF at −10° C. during 5 minutes under nitrogen environment. The reaction mixture was stirred for 30 minutes. Then, 2-fluorophenyl isocyanate (352 mg/ml, 3.14 mM) was added to the stirring reaction mixture. The mixture was stirred further for 3 hours during which the temperature was allowed to reach the room temperature (37° C.). The reaction mixture was quenched with water, diluted with water, extracted with ethyl acetate and dried over sodium sulphate. The combined fractions of ethyl acetate were concentrated under vacuum and chromatographed using ethyl acetate:hexane (1:49) to afford the pure compound 8l as oil. Yield: 580 mg, 63.03%.

Workup

  1. stirringThe mixture was stirred further for 3 hours during which the temperature
  2. customthe room temperature (37° C.)
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulphate
  7. concentrationThe combined fractions of ethyl acetate were concentrated under vacuum
  8. customchromatographed

Sources & evidence

ORD record
ord-4978a5fc275242ee9eb5099276d86ce5
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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