O-Phenylenediamine → 3-(1H-Benzo[D]imidazol-2-YL)-5-iodo-1H-indazole

HRID 218462Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20]>CN(C=O)C.CCOC(C)=O>[NH:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]=[C:11]1[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([I:1])[CH:3]=2)[NH:7][N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-iodo-1H-indazole-3-carboxaldehyde (544 mg, 2 mmol) and 1,2-diaminobenzene (216 mg, 2 mmol) in DMF (5 mL) was add 4 Å molecular sieves. The mixture was kept at 60° C. for 2 hr, then the mixture was heated up to 80° C. overnight under air atmosphere (air balloon). The mixture was diluted with EtOAc, washed with water, dried and concentrated. The crude product was purified by flash chromatography to afford 3-(1H-benzimidazol-2-yl)-5-iodo-1H-indazole (500 mg, 69%).

Workup

washwashed with water
customdried
concentrationconcentrated
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-c278e190bd6f4c35aa8e11db80884e08
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198456B2

Reaction notes

Loading…