Sodium Carbonate → N-[6-(1-Methyl-1H-indol-5-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1616044Notes

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.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][C:26](B(O)O)=[CH:27][CH:28]=2)[CH:23]=[CH:22]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]>[CH3:20][N:21]1[C:29]2[C: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][CH:28]=2)[CH:23]=[CH:22]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(6-bromo-1H-indazol-4-yl)-2-pyridinecarboxamide (100 mg, 0.31 mmol), (1-methyl-1H-indol-5-yl)boronic acid (65 mg, 0.37 mmol, available from Apollo), Pd(dppf)Cl2 (10 mol %, 31 mg, 0.038 mmol), aqueous sodium carbonate solution (2M, 0.468 ml, 0.94 mmol) in dioxane/water 1:1 (3 ml) was heated at 150° C. for 30 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 HPLC using the following conditions to provide the title compound (15 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 HPLC

Sources & evidence

ORD record: ord-5dcd2d51eecf4467bb48921b84e974d9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765743B2

Reaction notes

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