Cesium carbonate → HCID 59382926, compound

HRID 2355317Notes

Reaction equation

HRID 2355317 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH:11]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2Br)[CH2:6]1)(=[O:4])=[O:3].C([O-])([O-])=O.[Cs+].[Cs+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:13]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:7]1[CH2:8][CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 59383011HCID 59383011, compound

Product 1

HCID 59382926HCID 59382926, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A tube designed for a microwave reactor was charged with 1-methanesulfonyl-3-((3-methoxypropoxy)(2-bromophenyl)methyl)piperidine (200 mg, 0.0.476 mmol, 1.0 equiv), PdCl2(dppf) (21 mg, 0.0.238 mmol, 0.05 equiv), Cs2CO3 (511 mg, 1.57 mmol, 3.3 equiv), phenylboronic acid (87 mg, 0.714 mmol, 1.5 equiv) and 4 mL of 1,4-dioxane. The tube was sealed and the resulting yellow solution degassed by three evacuates/N2 backfill cycles, then placed in a microwave reactor and heated to 120° C. for 15 min. The contents were transferred to a flask and volatile materials removed in vacuo. The residue was partitioned between CH2Cl2 and water. The yellow organic layer was washed with brine, dried over Na2SO4 and evaporated. The product was purified by flash chromatography on 4 g silica, eluting with 0 to 50% EtOAc in hexanes. 3-(Biphenyl-2-yl(3-methoxypropoxy)methyl)-1-(methylsulfonyl)piperidine was isolated as an off white solid (82 mg, 91%). 1H NMR (CDCl3) δ 0.8-1.8 (m, 8H), 2.25-2.5 (m, 4H), 2.85 (s, 3H), 3.25-3.55 (m, 4H), 3.25 (s, 3H), 3.55 and 3.62 (bd, 1H), 4.08 and 4.13 (d, 1H), 7.07-7.56 (m, 9H).

Workup

  1. customA tube designed for a microwave reactor
  2. customThe tube was sealed
  3. customthe resulting yellow solution degassed by three evacuates/N2 backfill cycles
  4. customplaced in a microwave reactor
  5. customThe contents were transferred to a flask
  6. customvolatile materials removed in vacuo
  7. customThe residue was partitioned between CH2Cl2 and water
  8. washThe yellow organic layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe product was purified by flash chromatography on 4 g silica
  12. washeluting with 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-8d94415203374a3f9a0d01eaad9bad08
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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