Carbon tetrabromide → HCID 53794214, compound

HRID 2185134Notes

Reaction equation

HRID 2185134 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[O:15][C:14]([P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:12]=3)[N:7]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:6]=2[C:5]([CH2:28][CH2:29][CH2:30][CH2:31]O)=[CH:4][C:3]=1[F:33].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:54]>C(Cl)Cl>[NH2:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[O:15][C:14]([P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:12]=3)[N:7]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:6]=2[C:5]([CH2:28][CH2:29][CH2:30][CH2:31][Br:54])=[CH:4][C:3]=1[F:33]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54030908HCID 54030908, compound

Product 1

HCID 53794214HCID 53794214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 1.0 mmol of 4-amino-7-(4-hydroxybutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole in 20 mL of CH2Cl2 was added 3.0 mmol of PPh3 and 3.0 mmol of CBr4. After 40 min. at room temperature solvent was removed and the residue was subjected to chromatography to give 4-amino-7-(4-bromobutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole. CCl4 gave the corresponding chloro compound.

Workup

  1. customAfter 40 min. at room temperature solvent was removed

Sources & evidence

ORD record
ord-f1e19db3c6be4b0bb48fb9f898f5ce76
Source dataset
uspto-grants-2002_06
Patent number
US06399782B1

Reaction notes

Loading…