Benzyl mercaptan → HCID 178513701, compound

HRID 1049875Notes

Reaction equation

HRID 1049875 reaction equation
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.Br[C:44]1[S:48][C:47]([NH:49][C:50]([C:52]2[CH:56]=[CH:55][NH:54][N:53]=2)=[O:51])=[C:46]([C:57](=[O:59])[NH2:58])[CH:45]=1.[C:60]1([CH2:66][SH:67])[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1.CCN(C(C)C)C(C)C>O1CCOCC1.C(Cl)Cl.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]>[CH2:66]([S:67][C:44]1[S:48][C:47]([NH:49][C:50]([C:52]2[CH:56]=[CH:55][NH:54][N:53]=2)=[O:51])=[C:46]([C:57](=[O:59])[NH2:58])[CH:45]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

8

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178513510HCID 178513510, compound

Product 1

HCID 178513701HCID 178513701, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of Pd2(dba)3 (20 mg, 0.022 mmol) and Xantphos (51 mg, 0.087 mmol) in 1,4-dioxane (5 mL) is degassed, put under N2 and sonicated. This mixture is then added to a degassed mixture of 1H-Pyrazole-3-carboxylic acid (5-bromo-3-carbamoyl-thiophen-2-yl)-amide (345 mg, 1.09 mmol), phenyl-methanethiol (135 μL, 1.15 mmol) and DIEA (380 μL, 2.18 mmol) in 1,4-dioxane (5 mL). Resulting mixture is stirred at 100° C. under N2. After 75 min, the reaction is diluted with DCM and washed with aqueous NaHCO3. The organic is then dried over MgSO4, filtered and evaporated to an oily residue. This residue is triturated in di-isopropylether, separated by filtration, the cake is dried, and the resulting the solid is used as such.

Workup

  1. customis degassed
  2. customsonicated
  3. customResulting mixture
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe organic is then dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to an oily residue
  8. customThis residue is triturated in di-isopropylether
  9. customseparated by filtration
  10. customthe cake is dried

Sources & evidence

ORD record
ord-79a532987da6400086bb7d74b899f9f8
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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