N-bromobutanimide → HCID 58972993, compound

HRID 1171058Notes

Reaction equation

HRID 1171058 reaction equation
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][Br:27])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 58972974HCID 58972974, compound

Product 1

HCID 58972993HCID 58972993, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the bis-tert-butoxycarbonyl-(7-methyl-isoquinolin-1-yl)amine (500 mg, 1.40 mmol), N-bromosuccinimide (265 mg, 1.47 mmol) and 4 mg of benzoyl peroxide in 10 mL of CCl4 was refluxed overnight. The solution was concentrated and loaded to a flash column using 10% EtOAc in hexane as eluent. This gave 440 mg (72% yield) of yellow solid product. 1H-NMR (300 MHz, CDCl3) δ 8.44(d, 1H), 7.94 (s, 1H), 7.87 (d, 1H), 7.73 (d, 1H), 7.64 (d, 1H), 4.64 (s, 2H), 1.32 (s, 18H); LC/MS (ESI): calcd mass 436.1. found 437.1 (MH)+.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-3eec951fe6bd4609ac614883dcb70f2d
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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