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2-(Tributylstannyl)pyridine → HCID 66599726, 화합물

HRID 1889037
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HRID 1889037 반응식
Br[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[N:4][N:3]=1
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6

반응물 2

HCID 6077842-(Tributylstannyl)pyridineHCID 17998723tert-butyl 3-bromo-5H,6H,7H,8H-(1,2,4)triazolo(4,3-a)pyrazine-7-carboxylate

생성물 1

HCID 66599726HCID 66599726, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
130 °C

실험 절차

To a solution of 1,1-dimethylethyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (200 mg, 0.660 mmol, commercially available) in 1,4-dioxane (2 mL), 2-(tributylstannanyl)pyridine (364 mg, 0.990 mmol) was added and mixture was degassed with a stream of argon for few minutes. Pd(Ph3P)4 (38.1 mg, 0.033 mmol) was then added followed by copper(I) iodide (39.2 mg, 0.206 mmol) and the mixture was submitted to microwave irradiation heating at 130° C. for 25 minutes until the reaction was complete by LCMS. Volatiles were removed under reduced pressure and the residue was purified by chromatography on silica gel (Snap 11 g NH column) eluting with a gradient from 0 to 100% ethyl acetate in iso-hexane (10CV) and then with 100% ethyl acetate (7CV). A colourless oil was obtained. The product was still impure and so was further purified by chromatography on silica gel (Si 5 g) eluting with a 80% ethyl acetate in iso hexane (5CV) and then with 10% MeOH in DCM (5 CV) then by chromatography on silica gel (Si column 5 g) eluting first with ethyl acetate (4CV) and then with 10% MeOH in DCM (6CV). Colourless oil was obtained of the desired product in 115 mg.

후처리

  1. custommixture was degassed with a stream of argon for few minutes
  2. customirradiation
  3. customVolatiles were removed under reduced pressure
  4. customthe residue was purified by chromatography on silica gel (Snap 11 g NH column)
  5. washeluting with a gradient from 0 to 100% ethyl acetate in iso-hexane (10CV)
  6. customA colourless oil was obtained
  7. customso was further purified by chromatography on silica gel (Si 5 g)
  8. washeluting with a 80% ethyl acetate in iso hexane (5CV)
  9. washwith 10% MeOH in DCM (5 CV) then by chromatography on silica gel (Si column 5 g) eluting first with ethyl acetate (4CV)

출처 및 근거

ORD 기록
ord-322492452dc841e2800bd4af71db8f0c
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501946B2

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