Diisopropylethylamine → HCID 66765112, compound

HRID 1466814Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7](Br)[CH:6]=1)[CH3:2].[CH2:15]([O:23][C:24](=[O:28])[CH2:25][CH2:26][SH:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])C.[CH:29](N(C(C)C)CC)(C)C.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>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]>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([S:27][CH2:26][CH2:25][C:24]([O:23][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:22][CH3:29])=[O:28])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

3-Bromo-4-methoxy-benzoic acid ethyl ester (1.61 g, 6.62 mmol) and isooctyl-3-mercaptopropionate (1.73 g, 7.95 mmol) were dissolved in dioxane (26 mL) and the mixture was sparged with N2 (g) for 10 minutes. Diisopropylethyl amine (2.31 mL, 13.25 mmol), Xanthphos (0.1917 g, 0.33 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.1517 g, 0.166 mmol) were added and the mixture was sparged with N2 (g) for 5 minutes. The reaction was then heated to 90° C. for 2 hours after which time it was filtered to remove solid impurities. The mixture was concentrated and the residue was purified on silica gel (0-40% EtOAc in hexanes) to give the title compound.

Workup

customthe mixture was sparged with N2 (g) for 10 minutes
customthe mixture was sparged with N2 (g) for 5 minutes
filtrationwas filtered
customto remove solid impurities
concentrationThe mixture was concentrated
customthe residue was purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ec88ccc5db564be69341524009f9268d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

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