Sodium Carbonate → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1616042Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])[CH:3]=1.[NH:20]1[C:28]2[C:23](=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:20]1[C:28]2[C:23](=[C:24]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][NH:8]4)=[C:4]([NH:11][C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=4)=[O:13])[CH:3]=3)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(6-bromo-1H-indazol-4-yl)-2-pyridinecarboxamide (38 mg, 0.12 mmol), 1H-indol-4-ylboronic acid (23 mg, 0.14 mmol, available from Apollo), Pd(dppf)Cl2 (10 mol %, 12 mg, 0.015 mmol), aqueous sodium carbonate solution (2M, 0.18 ml, 0.36 mmol) in dioxane/water 1:1 (2 ml) was heated at 150° C. for 30 mins under microwave irradiation. The reaction mixture was filtered through a silica cartridge eluting with MeOH, then the solvent was removed in vacuo. Purification by mass directed preparative HPLC (Method B) give after evaporation of solvents the title compound as a light brown solid (21 mg).

Workup

filtrationThe reaction mixture was filtered through a silica cartridge
washeluting with MeOH
customthe solvent was removed in vacuo
customPurification by mass
customgive
customafter evaporation of solvents the title compound as a light brown solid (21 mg)

Sources & evidence

ORD record: ord-9f550ca3a76d4cadb710f4f9dff69423
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765743B2

Reaction notes

Loading…