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Cesium carbonate → cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 1809110
Notes
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Reaction equation

HRID 1809110 reaction equation
[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([CH2:18][C:19]#[N:20])[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([C:18]3([C:19]#[N:20])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 86646716cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile

Product 1

HCID 86646717cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrileYield 32.8%

Reagents, catalysts & solvents 3

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile (0.049 g, 0.17 mmol) and 1-bromo-2-(2-bromo-ethoxy)-ethane (0.04 g, 0.17 mmol) and caesium carbonate (1.0 mmol) in DMSO (2 mL) was stirred for 12 hr at room temperature. The mixture was diluted with water (5 mL) and DCM (5 mL). The organic layer was filtered and then evaporated to give an oil which was purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.02 g). LCMS m/z 359.24 [M+H]+ RT=10.70 min (Analytical Method 2).

Workup

  1. filtrationThe organic layer was filtered
  2. customevaporated
  3. customto give an oil which
  4. customwas purified by HPLC
  5. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-d72f4e5fb04846bea7151a0e61ee5e1c
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362008B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes