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Tetrahydrofuran → HCID 59828851, compound

HRID 1190991
Notes
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Reaction equation

HRID 1190991 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([C:23]#[CH:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C.C1COCC1>C([O-])(O)=O.[Na+].CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([C:24]#[C:23][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 15449580Tert-butyl [(6-chloropyridin-3-yl)methyl]carbamate

Product 1

HCID 59828851HCID 59828851, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8857Ethyl AcetateSolvent
HCID 516892Sodium BicarbonateSolvent

Procedure

Under a nitrogen atmosphere, add 3-(tert-butoxycarbonylamino-methyl)-6-chloropyridine (1 g, 4.12 mmol), cyclohexylacetylene (0.446 g, 4.12 mmol), dichlorobis(triphenylphosphine)-palladium (578 mg, 0.824 mmol), copper(I) iodide (157 mg, 0.824 mmol) and triethylamine (8.6 mL, 6.18 mmol) to THF (20 mL). Heat the mixture to reflux overnight. Cool the mixture to room temperature, and dilute with saturated aqueous NaHCO3 (50 mL) and EtOAc (50 mL). Separate the layers and extract the aqueous layer with EtOAc (4×30 mL). Wash the combined organic extracts with brine (20 mL), dry over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 6:1 gradient over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (0.71 g, 55%). MS (APCI+) m/z: 215 (M-Boc+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux overnight
  3. customSeparate the layers
  4. extractionextract the aqueous layer with EtOAc (4×30 mL)
  5. washWash the combined organic extracts with brine (20 mL)
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge)
  10. washeluting with hexane/EtOAc (1:0 to 6:1 gradient over 1.25 h, 80 mL/min)

Sources & evidence

ORD record
ord-1340c314287e4496b234e943d1d7bd60
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes