Potassium Carbonate → 5-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-indazole

HRID 879544

Reaction equation

[Br:1][C:2]1[C:3]([CH3:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.Br[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)[C:3]([CH3:9])=[N:4][CH:5]=1.[Br:1][C:2]1[CH:7]=[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[N:16]=[CH:15]3)[CH:5]=[N:4][C:3]=1[CH3:9]

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of 3,5-dibromo-2-methylpyridine (1.0 g, 3.99 mmol) and 5-(bromomethyl)-1-methyl-1H-indazole (772 mg, 4.38 mmol) in 1,4-dioxane (12 mL) was added Pd(PPh3)4 (231 mg, 0.20 mmol) and potassium carbonate solution (2 M aqueous, 6 mL, 12 mmol). The reaction mixture was stirred at 105° C. in a sealed tube for 1.5 h. The mixture was diluted with water (15 mL) and EtOAc (20 mL). The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by CombiFlash (EtOAc w/5% MeOH and Hexanes) to give 5-(5-bromo-2-methylpyridin-3-yl)-1-methyl-1H-indazole and 5-(5-bromo-6-methylpyridin-3-yl)-1-methyl-1H-indazole.

Workup

customThe layers were separated
customthe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by CombiFlash (EtOAc w/5% MeOH and Hexanes)

Sources & evidence

ORD record: ord-ca3fabd5a2aa4e58945490cc7b3a090f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Linked notes

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