N-bromobutanimide → HCID 90285707, compound

HRID 1050647Notes

Reaction equation

HRID 1050647 reaction equation
[CH3:1][C:2]1([CH3:37])[C:11]2=[CH:12][C:13]([B:23]3[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]3)=[CH:14][C:15]3[C:16]([CH3:22])([CH3:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:7]5[C:8]=4[N:9]([C:10]=32)[C:4]2[C:5](=[CH:34][CH:35]=[CH:36][C:3]1=2)[C:6]5([CH3:33])[CH3:32].[Br:38]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:38][C:19]1[CH:18]=[C:17]2[C:16]([CH3:21])([CH3:22])[C:15]3[CH:14]=[C:13]([B:23]4[O:24][C:25]([CH3:31])([CH3:30])[C:26]([CH3:29])([CH3:28])[O:27]4)[CH:12]=[C:11]4[C:2]([CH3:37])([CH3:1])[C:3]5[C:4]6[N:9]([C:10]=34)[C:8]2=[C:7]([C:6]([CH3:33])([CH3:32])[C:5]=6[CH:34]=[CH:35][CH:36]=5)[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90285418HCID 90285418, compound

Product 1

HCID 90285707HCID 90285707, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4,4,8,8,12,12-hexamethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (2.10 g, 4.27 mmol) in CHCl3 (77 mL) at 0° C. was added N-bromosuccinimide (0.761 g, 4.27 mmol) over a period of 20 min. While warming up to room temperature, the resulting solution was stirred in the absence of light overnight. The reaction was quenched with a saturated aqueous solution of Na2S2O3. The resulting mixture was extracted with CH2Cl2 (3×) and the combined organic fractions were dried with MgSO4. After filtration and evaporation of the solvent, the residue was subjected to column chromatography (silica, n-hexane/CH2Cl2 2:3). Final recrystallization from ethanol yielded 2-bromo-4,4,8,8,12,12-hexamethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine as a white powder (1.87 g, 77%).

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of Na2S2O3
  2. extractionThe resulting mixture was extracted with CH2Cl2 (3×)
  3. dry with materialthe combined organic fractions were dried with MgSO4
  4. filtrationAfter filtration and evaporation of the solvent
  5. customFinal recrystallization from ethanol

Sources & evidence

ORD record
ord-b43026b1f09c4cca907d127cda863c36
Source dataset
uspto-grants-2016_07
Patent number
US09385326B2

Reaction notes

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