Benzyl mercaptan → HCID 86687539, compound

HRID 1473485Notes

Reaction equation

HRID 1473485 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[C:4]([CH3:13])[CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[CH2:65]([SH:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:65]([S:72][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[C:4]([CH3:13])[CH:3]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86687536HCID 86687536, compound

Product 1

HCID 86687539HCID 86687539, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a vial charged with 7-bromo-4-chloro-5-methylquinoline (0.048 g, 0.187 mmol) was added Xantphos (0.022 g, 0.037 mmol), Pd2(dba)3 (0.017 g, 0.019 mmol), dioxane (0.748 ml), DIEA (0.065 ml, 0.374 mmol) and benzyl mercaptan. The mixture was purged with argon and heated to 60° C. overnight. The mixture was directly loaded onto a 25 HP silicycle column and purified by ramping EtOAc in heptane (0 to 50%, 10% DCM throughout) to provide product as a light yellow solid (35 mg, 62%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.97 (s, 3H) 4.31 (s, 2H) 7.22-7.26 (m, 1H) 7.27-7.31 (m, 1H) 7.31-7.39 (m, 3H) 7.44 (d, J=6.94 Hz, 2H) 7.82 (d, J=1.96 Hz, 1H) 8.61 (d, J=4.70 Hz, 1H). m/z (ESI) 300.2 (M+H)+.

Workup

  1. customThe mixture was purged with argon
  2. custompurified

Sources & evidence

ORD record
ord-9e3f841232014f8ca26f53d730fed5a7
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…