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

HRID 1616043Notes

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](=[CH:24][CH:25]=[C:26](B(O)O)[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](=[CH:24][CH:25]=[C:26]([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: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 (70 mg, 0.22 mmol), 1H-indol-6-ylboronic acid (42 mg, 0.26 mmol), Pd(dppf)Cl2 (10 mol %, 22 mg, 0.027 mmol), aqueous sodium carbonate solution (2M, 0.328 ml, 0.656 mmol) in dioxane/water 1:1 (3 ml) was heated at 150° C. for 15 mins under microwave irradiation. The reaction mixture was filtered through a silica cartridge eluting with MeOH. The solvent was removed in vacuo. The crude compound obtained was purified by mass directed preparative HPLC (Method B) to afford the title compound (9 mg).

Workup

filtrationThe reaction mixture was filtered through a silica cartridge
washeluting with MeOH
customThe solvent was removed in vacuo
customThe crude compound obtained
customwas purified by mass

Sources & evidence

ORD record: ord-42f9a906265241cebb87ea3e92f4ddb3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765743B2

Reaction notes

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