Sodium Carbonate → 8-(3-Chloro-5-phenyl-4-pyridinyl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1622378Notes

Reaction equation

HRID 1622378 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:19])[C:7]=1[N:8]1[CH2:18][CH2:17][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(#N)C>[Cl:19][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]=1[N:8]1[CH2:18][CH2:17][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 45275674HCID 45275674, compound

Product 1

HCID 452756758-(3-Chloro-5-phenyl-4-pyridinyl)-2,8-diazaspiro[4.5]decan-1-oneYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure E was followed using 8-(3,5-dichloropyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one E59 (38 mg, 0.13 mmol), phenyl boronic acid (19 mg, 0.16 mmol), tetrakis(triphenylphosphine)palladium(0) (7.3 mg, 5 mol %), acetonitrile (1.4 ml) and 0.5 M sodium carbonate (0.35 ml, 0.18 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 97:3) followed by preparative hplc (CH3CN, H2O, gradient 1:9 to 9:1) to furnish the title compound as a white solid (12 mg, 28%), along with recovered starting material as a clear colourless oil (10 mg, 23% RSM), LC-MS (ESI, 4 min) Rt 2.22 min, m/z 342 (100%, [M+H]+); m/z (ESI) C19H20N3ClO requires 341.1295, found [M+H]+ 341.1301.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 97:3)

Sources & evidence

ORD record
ord-a22bd348f7f44df29838dd2714c8308b
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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