Cesium carbonate → Tert-butyl 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate

HRID 588420ノート

反応式

HRID 588420 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1.[C:17](=[O:24])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH2:18].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:20]([O:19][C:17](=[O:24])[NH:18][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1)([CH3:23])([CH3:22])[CH3:21]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 717439846-Bromo-2-(pyridin-3-YL)-[1,2,4]triazolo[1,5-A]pyridine

生成物 1

HCID 89464387Tert-butyl 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate収率 72.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 6-bromo-2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine (1.65 g, 6.00 mmol), tert-butyl carbamate (843 mg, 7.2 mmol) and cesium carbonate (2.74 g, 8.4 mmol) in 1,4-dioxane (37.8 ml) was purged with argon. Then tris(dibenzylideneacetone)dipalladium(0) (330 mg, 360 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (416 mg, 720 μmol) were added and the purging was repeated. The mixture was heated to reflux and stirred for 18 hours under argon atmosphere. After evaporation to dryness under reduced pressure, the crude material was purified by flash chromatography (50 g silicagel column using heptane/ethyl acetate 20-100% as eluent). Final evaporation of the solvents afforded (2-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-carbamic acid tert-butyl ester (1.35 g, 72.5%) as yellow solid. Mp.: 296° C. MS: m/z=312.3 (M+H+).

後処理

  1. customwas purged with argon
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. customAfter evaporation to dryness under reduced pressure
  5. customthe crude material was purified by flash chromatography (50 g silicagel column using heptane/ethyl acetate 20-100% as eluent)
  6. customFinal evaporation of the solvents

出典と根拠

ORDレコード
ord-4f093fc78e5e46c8befeab98410224a8
出典データセット
uspto-grants-2016_01
特許番号
US09227970B2

反応ノート

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