Cesium carbonate → 6-(3-Fluorophenyl)-N-pyridin-3-yl-5-pyridin-4-ylpyrazin-2-amine

HRID 1710704Notes

Reaction equation

HRID 1710704 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1.Br[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH:14][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:11]=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 160715396-(3-Fluorophenyl)-5-pyridin-4-ylpyrazin-2-amine

Product 1

HCID 160718986-(3-Fluorophenyl)-N-pyridin-3-yl-5-pyridin-4-ylpyrazin-2-amineYield 69.3%

Reagents, catalysts & solvents 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 6-(3-fluorophenyl)-5-pyridin-4-ylpyrazin-2-amine (Example 1, 100 mg, 0.37 mmol), 3-bromopyridine (43 μL, 0.45 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (17 mg, 0.03 mmol), cesium carbonate (171 mg, 0.52 mmol) and dioxane (2 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzilideneacetone) dipalladium (14 mg, 0.01 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 20 h, the mixture was cooled and water was added. The solid was collected by filtration, washed with water, diethyl ether and dried, to give the title compound as a yellow solid (88 mg, 63%).

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 100° C.
  5. temperaturethe mixture was cooled
  6. filtrationThe solid was collected by filtration
  7. washwashed with water, diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-892f8d33855a4fcf9d5ff5fbc9836aeb
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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