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

HRID 588420노트

반응식

HRID 588420 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-4f093fc78e5e46c8befeab98410224a8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227970B2

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