Allyl bromide → HCID 59300879, compound

HRID 2235444Notes

Reaction equation

HRID 2235444 reaction equation
[CH3:1][C:2]1([CH3:26])[C:10]2[C:5](=[CH:6][C:7]([N+:22]([O-])=O)=[C:8]([NH:11][C:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[NH:4][C:3]1=[O:25].[CH2:27](Br)[CH:28]=[CH2:29].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CN(C)C=O>[CH2:29]([N:4]1[C:5]2[CH:6]=[C:7]3[N:22]=[C:12]([C:13]4[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=4)[NH:11][C:8]3=[CH:9][C:10]=2[C:2]([CH3:26])([CH3:1])[C:3]1=[O:25])[CH:28]=[CH2:27]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 23092680HCID 23092680, compound

Product 1

HCID 59300879HCID 59300879, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)4-methoxy-benzamide (200 mg), allyl bromide (78 mg; 0.65 mmol) and K2CO3 (233 mg; 1.69 mmol) in acetone (3.2 ml) and N,N-dimethylformamide (1.6 ml) is stirred at 50° C. for 48 h. The mixture is filtered and concentrated in vacuo. The residue is suspended in acetic acid (3 ml), iron (150 mg; powder) is added and the resulting mixture is heated in a microwave apparatus at 150° C. for 900 s. After re-cooling the mixture is filtered and concentrated in vacuo. The desired compound is obtained by preparative RP-HPLC.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. additioniron (150 mg; powder) is added
  4. temperatureAfter re-cooling the mixture
  5. filtrationis filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bd9a358d17e48aeb093ce5ceb08ba5f
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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