Sodium Hydroxide → 5-(1H-indol-4-yl)pyridin-2-amine

HRID 988136Notes

Reaction equation

[OH-].[Na+].CC1(C)C(C)(C)OB([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)O1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][N:23]=1>[Pd].C1COCC1>[NH:15]1[C:16]2[C:12](=[C:11]([C:25]3[CH:26]=[CH:27][C:22]([NH2:21])=[N:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

Palladium catalyst Pd(PPh3)4 (142 mg, 0.12 mmol) and freshly prepared aqueous sodium hydroxide (493 mg, 12.33 mmol in 6 mL of water) were added to a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (1 g, 4.11 mmol) and 2-amino-5-bromopyridine (853 mg, 4.93 mmol) in THF (20 mL). The system was degassed and then purged three times with nitrogen. The mixture was stirred under nitrogen at 80° C. in an oil bath for 4.5 hours. It was then cooled to room temperature and ethyl acetate (300 mL) was added. The organic layer was isolated, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give 720 mg (84%) of 5-(1H-indol-4-yl)-pyridin-2-ylamine as a thick brown syrup.

Workup

customThe system was degassed
custompurged three times with nitrogen
temperatureIt was then cooled to room temperature
additionethyl acetate (300 mL) was added
customThe organic layer was isolated
washwashed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-54024d6cac784896b0dc2381929bf3ef
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635640B2

Reaction notes

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