Benzyl Bromide → HCID 22222296, compound

HRID 1794604Notes

Reaction equation

HRID 1794604 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH2:12][CH2:13][CH3:14])=[N:6][C:5]=2[S:4][N:3]=1.[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O>[CH2:21]([N:8]1[C:9](=[O:11])[C:10]2[C:2]([CH3:1])=[N:3][S:4][C:5]=2[N:6]=[C:7]1[CH2:12][CH2:13][CH3:14])[C:18]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 135677718HCID 135677718, compound

Product 1

HCID 22222296HCID 22222296, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 30 (730 mg, 3.5 mmol) in dioxane (10 mL) was added BnBr (830 μl, 7 mmol) and Cs2CO3 (1.6 g, 4.9 mmol). The reaction mixture was stirred at room temperature over night, then diluted with EtOAc, washed with water, dried and purified by silica gel column chromatography to give 31 (430 mg, 42%). 1H-NMR (400 MHz, CDCl3): δ 7.15–7.40 (m, 5H), 5.40 (s, 2H), 2.84 (s, 3H), 2.75 (t, J=7.61 Hz, 2H), 1.80 (m, 2H), 0.99 (t, J=7.38 Hz, 3H).

Workup

  1. washwashed with water
  2. customdried
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d9fabeafcb824c38a6d697ad114f060a
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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