Potassium Carbonate → HCID 178505929, compound

HRID 45948

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH2:15]Br.C([O-])([O-])=O.[K+].[K+]>>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([F:20])[CH:19]=1)[CH2:15][N:10]([CH2:15][C:14]1[CH:13]=[C:12]([F:11])[CH:19]=[C:18]([F:20])[CH:17]=1)[C:8]1[CH:7]=[CH:6][C:5]2[NH:1][CH:2]=[N:3][C:4]=2[CH:9]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 136235-Aminobenzimidazole

HCID 5188963,5-Difluorobenzyl bromide

Product 1

HCID 178505929HCID 178505929, compound

Procedure

The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 3,5-difluorobenzylbromide (455 mg; 0.285 ml; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.065 g (16.7%); MS m/z: 386.3 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.75 (s, 4H); 6.67-6.70 (m, 2H); 6.97-6.99 (m, 4H); 7.07 (tt, 2H, 4J=2.3 Hz, 3JH,F=9.3 Hz); 7.36-7.37 (m, 1H); 7.94 (s, 1H); 11.96 (br s, 1H); HPLC (METHOD [A]): rt 16.26 min (100%)

Workup

customThe compound was synthesized
customrt 16.26 min (100%)

Sources & evidence

ORD record: ord-c37a9bf8caf740f4aa8b27a7026f2c83
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541596B2

Linked notes

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