N-bromobutanimide → HCID 53855313, compound

HRID 1281672Notes

Reaction equation

HRID 1281672 reaction equation
[Cl:1][C:2]1[C:28]([CH3:29])=[CH:27][C:5]2[N:6]([C@@H:9]3[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]3[O:11][C:12](=[O:14])[CH3:13])[CH:7]=[N:8][C:4]=2[CH:3]=1.[Br:30]N1C(=O)CCC1=O>O1CCCC1>[Br:30][C:7]1[N:6]([C@@H:9]2[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[C:5]2[CH:27]=[C:28]([CH3:29])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69946643HCID 69946643, compound

Product 1

HCID 53855313HCID 53855313, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Procedure IV using) 5-Chloro-6-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.12 g, 0.28 mmol), 20 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 2.0 g (11 mmol) of N-bromosuccinimide that was added over 2 h. The product from work-up by General Procedure IV was partially purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 0.5% methanol to give 2-Bromo-5-chloro-6-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.097 g) of sufficient purity for the next step; 1H NMR (DMSO-d6) δ7.99 (s,1H), 7.66 (s, 1H), 5.93-5.90 (d, 1H, J=8.9 Hz), 5.69-5.62 (m, 3H), 4.02-3.92 (m, 2H), 2.41 (s, 3H), 2.20 (s, 3H), 1.99 (s, 3H), 1.73 (s, 3H).

Workup

  1. customThe title compound was prepared
  2. customThe product from work-up by General Procedure IV was partially purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 0.5% methanol

Sources & evidence

ORD record
ord-eca6822f749443db883b3d8e2337557f
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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