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2-(Tributylstannyl)pyridine → HCID 66599726, compound

HRID 1889037
Notes
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Reaction equation

HRID 1889037 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

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

Product 1

HCID 66599726HCID 66599726, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-322492452dc841e2800bd4af71db8f0c
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501946B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes