Potassium Carbonate → 2-Methoxy-5-(1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)pyridin-3-amine

HRID 711385Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:12]([CH3:15])=[N:13][N:14]=3)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[C:23]([NH2:24])=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[CH3:16][O:17][C:18]1[C:23]([NH2:24])=[CH:22][C:21]([C:2]2[CH:11]=[C:10]3[C:5]([N:6]=[CH:7][C:8]4[N:9]3[C:12]([CH3:15])=[N:13][N:14]=4)=[CH:4][CH:3]=2)=[CH:20][N:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of crude 8-bromo-1-methyl-[1,2,4]triazolo[4,3-a]quinoxaline (809 mg, 3.07 mmol), PdCl2(dppf)2 (132.6 mg, 0.153 mmol), 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (1 g, 4.3 mmol) and K2CO3 (1.7 g, 12.28 mmol) in DMF (40 mL) and water (15 mL) was stirred at 100° C. overnight. Half of solvent was removed. After cooling to room temperature, the resulting mixture was poured into ice-water. The precipitate was collected, washed with water three times, and dried in vacuo to afford crude 2-methoxy-5-(1-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)pyridin-3-amine as grey solid (730 mg, yield 77%) which was used in next step without further purification. MS (m/z): 307 (M+H)+.

Workup

customHalf of solvent was removed
temperatureAfter cooling to room temperature
additionthe resulting mixture was poured into ice-water
customThe precipitate was collected
washwashed with water three times
customdried in vacuo

Sources & evidence

ORD record: ord-0e97e70b03c54d1399a8d9e6548f7209
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181264B2

Reaction notes

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