Sodium hydride → HCID 60161675, compound

HRID 1843304Notes

Reaction equation

HRID 1843304 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[H-].[Na+].[CH:17]([N:20]([CH:24]([CH3:26])[CH3:25])[C:21](Cl)=[O:22])([CH3:19])[CH3:18]>O1CCCC1.C(OCC)(=O)C>[CH:17]([N:20]([CH:24]([CH3:26])[CH3:25])[C:21](=[O:22])[O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][CH2:5][N:4]2[CH2:1][C:2]#[CH:3])=[CH:9][CH:10]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 87890Diisopropylcarbamoyl chlorideHCID 86704185HCID 86704185, compound

Product 1

HCID 60161675HCID 60161675, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(prop-2-ynyl)-1,2,3,4-tetrahydroquinolin-7-ol (400 mg, 2.14 mM) in dry tetrahydrofuran (THF; 5 mL) was added to the stirred solution of sodium hydride in dry THF at −10° C. during 5 minutes under nitrogen environment at room temperature (25° C.). The reaction, mixture was stirred for 30 minutes. Then, N,N-diisopropyl carbamoyl chloride (510 mg) was added to the stirring reaction mixture. The mixture was stirred further for 7 hours during which the temperature was allowed to reach the room temperature (35° C.). The reaction mixture was diluted with ethyl acetate, washed with water, 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 10h as semisolid. Yield: 72.6%.

Workup

  1. customThe reaction, mixture
  2. stirringThe mixture was stirred further for 7 hours during which the temperature
  3. customthe room temperature (35° C.)
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationThe combined fractions of ethyl acetate were concentrated under vacuum
  7. customchromatographed

Sources & evidence

ORD record
ord-e212f3b695a04e2c84511f6897927455
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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