N-bromobutanimide → HCID 58124863, compound

HRID 1971704Notes

Reaction equation

HRID 1971704 reaction equation
[C:1]([N:5]1[CH2:25][CH2:24][CH2:23][C:8]2[CH:9]=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:26])([CH3:4])([CH3:3])[CH3:2].[Br:27]N1C(=O)CCC1=O>CN(C=O)C.O>[C:1]([N:5]1[CH2:25][CH2:24][CH2:23][C:8]2[C:9]([Br:27])=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 581248159-tert-butyl-2-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

Product 1

HCID 58124863HCID 58124863, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 340 mg of 13b in 3 ml of DMF was added in small portions 160 mg of N-bromosuccinimide. After stirring for an additional 15 minutes the reaction mixture was diluted with 3 ml of water and stirred for an additional 15 minutes. The precipitate was filtered and dried, to give 380 mg of 13c, as white crystalline material. Mp: 218-220° C. MS-ESI: [M+1] 495.06, 497.06, 499.08. NMR (CDCl3) δ 1.53 (s, 9, tertC4H9), 1.95 (m, 2, CH2), 2.71 (t, 2, CH2), 2.97 (t, 2, CH2), 3.38 (t, 2, CH2), 4.45 (t, 2, CH2) 6.77, 8.56 (2×s, 2, Ar—H).

Workup

  1. stirringstirred for an additional 15 minutes
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-09d5122da94c432bab7eb37d94cbf18b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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