Diisopropylethylamine → HCID 90327362, compound

HRID 1471638Notes

Reaction equation

HRID 1471638 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C@H:9]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:30](=[S:33])([O-:32])[CH3:31].[K+].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>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:30](=[O:32])([S:33][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C@H:9]([NH:22][C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:29])[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])=[O:11])[CH:3]=1)[CH3:31]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23670855Potassium ethanethioateHCID 90289952HCID 90289952, compound

Product 1

HCID 90327362HCID 90327362, compoundYield 65%

Reagents, catalysts & solvents 2

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

Procedure

A solution of (5)-tert-butyl 3-(3-bromophenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (464 mg, 1.0 mmol), potassium ethanethioate (171.3 mg, 1.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (46 mg, 0.05 mmol), xantphos (58 mg, 0.1 mmol) and DIPEA (0.35 ml, 2 mmol) in 1,4-dioxane (4 ml) was heated at 150° C. for 20 minutes in a microwave reactor. The mixture was filtered through celite and the celite was washed with EtOAc (2×50 ml). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (20-45% EtOAc/hexanes) to provide the desired product (300 mg, 0.65 mmol), 65%. MS (m/z) 459 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe celite was washed with EtOAc (2×50 ml)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was introduced to a silica gel loading column
  7. custompurified by column chromatography (20-45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6113689845a743ea955fa332f57a343a
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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