Ethanethiol → HCID 86707541, compound

HRID 339054Notes

Reaction equation

HRID 339054 reaction equation
CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:44]1[CH:53]=[C:52]2[C:47]([CH:48]=[CH:49][C:50]([C:54]3[N:58]4[CH:59]=[C:60]([C@@H:63]([N:68]5[CH2:72][CH2:71][C@H:70]([NH:73][C:74](=[O:80])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])[CH2:69]5)[C:64]([F:67])([F:66])[F:65])[CH:61]=[CH:62][C:57]4=[N:56][N:55]=3)=[N:51]2)=[CH:46][CH:45]=1.[CH2:81]([SH:83])[CH3:82].CCN(C(C)C)C(C)C>O1CCOCC1.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].C(Cl)(Cl)Cl>[CH2:81]([S:83][C:44]1[CH:53]=[C:52]2[C:47]([CH:48]=[CH:49][C:50]([C:54]3[N:58]4[CH:59]=[C:60]([C@@H:63]([N:68]5[CH2:72][CH2:71][C@H:70]([NH:73][C:74](=[O:80])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])[CH2:69]5)[C:64]([F:67])([F:66])[F:65])[CH:61]=[CH:62][C:57]4=[N:56][N:55]=3)=[N:51]2)=[CH:46][CH:45]=1)[CH3:82]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86707542HCID 86707542, compound

Product 1

HCID 86707541HCID 86707541, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of Pd2 dba3-CHCl3 (13.1 mg, 0.0127 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (14.7 mg, 0.0254 mmol), tert-butyl (S)-1-((R)-1-(3-(7-bromo quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (150 mg, 0.254 mmol), ethanethiol (31.5 mg, 0.507 mmol), DIEA (98.3 mg, 0.761 mmol) in dioxane was heated to 150° C. under microwave irradiation for 1 hour. After cooling, the reaction was concentrated under reduced pressure and purified by chromatography (SP4, 12M, eluting with a gradient of water/ACN 100:0 to 0:100, 30 column volumes) to yield tert-butyl (S)-1-((R)-1-(3-(7-(ethylthio)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (95 mg, 65.4% yield) as an oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction was concentrated under reduced pressure
  3. custompurified by chromatography (SP4, 12M
  4. washeluting with a gradient of water/ACN 100:0 to 0:100, 30 column volumes)

Sources & evidence

ORD record
ord-84002cb082934f5c8963267e6dad1184
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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