Sodium Formate → 3-(1H-benzimidazol-2-yl)-1H-indazole-5-carboxaldehyde

HRID 218463Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](I)[CH:17]=2)[NH:12][N:11]=1.[CH:20]([O-])=[O:21].[Na+]>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:20]=[O:21])[CH:17]=2)[NH:12][N:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3-(1H-benzimidazol-2-yl)-5-iodo-1H-indazole (500 mg, 1.39 mmol) was dissolved in DMF (5 mL), then Pd(PPh3)2Cl2 (24 mg, 0.034 mmol) and sodium formate (142 mg, 2.1 mmol) were added. The reaction mixture was put under vacuum and recharged with CO three times, then heated up to 90° C. for 4 hr. The mixture was diluted with EtOAc, washed with brine, dried and concentrated. The crude product was purified by flash chromatography to afford 3-(1H-benzimidazol-2-yl)-1H-indazole-5-carboxaldehyde (135 mg, 37%) as yellow solid.

Workup

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

Sources & evidence

ORD record: ord-3c75f4f93bc749b98db430601a9902e9
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198456B2

Reaction notes

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