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

HRID 2276771
Notes
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Reaction equation

HRID 2276771 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 866868246-(5-Bromo-2-fluorophenyl)-N-(2-(2-fluorophenyl)propan-2-yl)-1,2,4-triazin-3-amine

Product 1

HCID 674538174-Fluoro-3-(3-(2-(2-fluorophenyl)propan-2-ylamino)-1,2,4-triazin-6-yl)benzonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

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

  1. washwashed with satd
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes