Sodium hydride → (S)-N-(5-(2-cyanobenzyloxy)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 473111Notes

Reaction equation

HRID 473111 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[H-].[Na+].Br[CH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>CN(C=O)C>[C:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2)#[N:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 70223136(S)-N-(5-(2-cyanobenzyloxy)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (0.098 mmol, 25 mg) and NaH (0.196 mmol, 4.70 mg) in DMF (1 mL) was stirred at room temp for 15 min. 2-(bromomethyl)benzonitrile (0.098 mmol, 19.20 mg) in DMF (1 mL) was added and the reaction mixture heated at 120° C. for 600 s in a Smith Synthesiser microwave. The reaction mixture was filtered through a Whatman filter and purified by preparative HPLC to give desired product (17.8 mg, 49.1%). MS (ESI): m/z [M−H]− 369.2

Workup

  1. temperaturethe reaction mixture heated at 120° C. for 600 s in a Smith Synthesiser microwave
  2. filtrationThe reaction mixture was filtered through a Whatman
  3. filtrationfilter
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4eb8095e17f34448817c5d2f3541f46b
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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