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

HRID 1710704ノート

反応式

HRID 1710704 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-892f8d33855a4fcf9d5ff5fbc9836aeb
出典データセット
uspto-grants-2010_09
特許番号
US07790728B2

反応ノート

読み込み中…