Dimethylformamide → N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-cyclopropylmethoxybenzamide

HRID 77414Notes

Reaction equation

HRID 77414 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.Br[CH2:23][CH:24]1[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:21])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:23][CH:24]3[CH2:26][CH2:25]3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 66663475HCID 66663475, compound

Product 1

HCID 66663484N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-cyclopropylmethoxybenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of N—((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-hydroxybenzamide (5.00 g), bromomethylcyclopropane (2.20 g), cesium carbonate (5.5 g) and DMF (50 ml) was heated to 75° C. for 12 hours. The cooled reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was washed three times with water, dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 400.32 (C21H22BrNO2); MS (ESI): 400 (M+H+).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product was thus obtained with the molecular weight of 400.32 (C21H22BrNO2)

Sources & evidence

ORD record
ord-056416edea0140658912cbf33774f3f0
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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