Dimethylformamide → 4-Fluoro-3-(3-(2-(2-fluorophenyl)propan-2-ylamino)-1,2,4-triazin-6-yl)benzonitrile

HRID 2276771Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:25])=[C:6]([C:8]2[N:13]=[N:12][C:11]([NH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])([CH3:17])[CH3:16])=[N:10][CH:9]=2)[CH:7]=1.[CH3:26][N:27](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.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>[F:25][C:5]1[CH:4]=[CH:3][C:2]([C:26]#[N:27])=[CH:7][C:6]=1[C:8]1[N:13]=[N:12][C:11]([NH:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])([CH3:17])[CH3:16])=[N:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-(5-Bromo-2-fluorophenyl)-N-(2-(2-fluorophenyl)propan-2-yl)-1,2,4-triazin-3-amine (2.2 g, 5.6 mmol), zinc cyanide (0.72 g, 6.2 mmol), Pd(PPh3)4 (2.9 g, 2.8 mmol), and DMF (20 mL) were combined and heated in a round bottom flask at 100° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with satd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered, concentrated and purified using silica gel chromatography to provide a yellow solid (1.7 g), m/z=352.1 [M+H].

Workup

washwashed with satd
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-1beef4ddbddd4f029fc3226b3daec02b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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