Cesium fluoride → 5-(3,5-Dimethyl-1,2-oxazol-4-yl)-6-(2-phenylethynyl)pyridin-2-amine

HRID 535422노트

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HRID 535422 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:16])=[N:6][C:7]=1[C:8]#[C:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:17][C:18]1[C:22](B(O)O)=[C:21]([CH3:26])[O:20][N:19]=1.[F-].[Cs+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C1COCC1>[CH3:17][C:18]1[C:22]([C:2]2[CH:3]=[CH:4][C:5]([NH2:16])=[N:6][C:7]=2[C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:21]([CH3:26])[O:20][N:19]=1

참가 물질

6

반응물 4

HCID 25953Cesium fluorideHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 866943675-Bromo-6-(2-phenylethynyl)pyridin-2-amine

생성물 1

HCID 866944115-(3,5-Dimethyl-1,2-oxazol-4-yl)-6-(2-phenylethynyl)pyridin-2-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A mixture of 5-bromo-6-(2-phenylethynyl)pyridin-2-amine B2a (20 g, 73 mmol), (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid (24 g, 170 mmol), CsF (44 g, 289 mmol) tris-(dibenzylideneacetone)dipalladium(0) (10.28 g, 11.2 mmol), tri-tert-butylphosphonium tetrafluoroborate (8.6 g, 296 mmol) and THF (200 ml) is stirred under argon atmosphere at 50° C. for 1 h. The mixture is filtrated and the precipitate washed with THF. The combined organic layers are concentrated in vacuo, diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 12.2 g (58%). HPLC-MS: M+H=290; tR=1.54 min (*Method—6).

후처리

  1. filtrationThe mixture is filtrated
  2. washthe precipitate washed with THF
  3. concentrationThe combined organic layers are concentrated in vacuo
  4. additiondiluted with DCM
  5. extractionextracted with a saturated aqueous solution of NaHCO3
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe product is purified by NP chromatography

출처 및 근거

ORD 기록
ord-b8f949b2d3a84c0999c8fdcb8451aca9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859541B2

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