Dimethylformamide → 2-(Methylsulfanyl)-7-(pyridin-2-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1262442Notes

Reaction equation

C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.CN(C)C=O.Br[C:17]1[N:25]2[C:20]([CH:21]=[N:22][C:23]([S:26][CH3:27])=[N:24]2)=[CH:19][CH:18]=1>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>[CH3:27][S:26][C:23]1[N:22]=[CH:21][C:20]2=[CH:19][CH:18]=[C:17]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[N:25]2[N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Trimethylstannanyl-pyridine (0.557 g, 2.30 mmol) in N,N-Dimethylformamide (7.6 mL, 98 mmol) was added 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.250 g, 1.02 mmol) and Tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.058 mmol) in a vial, and the mixture was heated in a block at 80° C. The reaction mixture was then diluted with EtOAc (30 mL) and washed with water (1×, 10 mL), 2.5M KF (2×, 10 mL), and brine (1×, 10 mL), followed by drying with sodium sulfate, filtering, and conc. in vacuo. The crude product was purified by ISCO column chromatography (0-25, 25-100% EtOAc/Hex) to give 2-Methylsulfanyl-7-pyridin-2-yl-pyrrolo[2,1-f][1,2,4]triazine (0.173 g, 70%). 1H-NMR (DMSO-d6): 9.09 (s, 1H), 8.71 (m, 2H), 7.98 (dt, 1H, J=7.80 Hz), 7.63 (d, 1H, J=4.74 Hz), 7.38 (dt, 1H, J=6.40), 7.12 (d, 1H, 4.98 Hz), 2.65 (s, 3H).

Workup

washwashed with water (1×, 10 mL), 2.5M KF (2×, 10 mL), and brine (1×, 10 mL)
dry with materialby drying with sodium sulfate
filtrationfiltering
customThe crude product was purified by ISCO column chromatography (0-25, 25-100% EtOAc/Hex)

Sources & evidence

ORD record: ord-0a6fa13ff4824781a4e2670a37f74dd5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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