Water → HCID 69081742, compound

HRID 594632Notes

Reaction equation

HRID 594632 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH:14]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=3[O:23][CH3:24])[CH2:13][CH2:12][CH2:11][C:10]2=[O:25])[CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:31]1[S:32][CH:33]=[CH:34][N:35]=1)CCC.O.CCOC(C)=O>C1COCC1.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>[CH3:24][O:23][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:15]=1[CH:14]1[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:31]3[S:32][CH:33]=[CH:34][N:35]=3)[CH:7]=2)[C:10](=[O:25])[CH2:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 86695637HCID 86695637, compound

Product 1

HCID 69081742HCID 69081742, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1-((2-bromopyridin-4-yl)methyl)-6-(2,6-dimethoxyphenyl)piperidin-2-one (43 mg; 0.10 mmol; compound corresponding to example 36), commercially available 2-(tributylstannyl)thiazole (144 mg; 0.38 mmol), and PdCl2(PPh3)2 (7.5 mg; 0.01 mmol) in anh. THF (3 ml) was heated to 75° C., under nitrogen, for 24 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.75 min.; [M+H]+: 410.00 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by preparative HPLC
  8. customafforded the target compound

Sources & evidence

ORD record
ord-2dc53060082e46daa77817236578d53f
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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