Cesium carbonate → HCID 58043775, compound

HRID 1919130Notes

Reaction equation

HRID 1919130 reaction equation
[C:1]12[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:8][C:7]1[C:6](=[O:14])[NH:5][CH2:4][CH2:3][C:2]2=1.[C:15]([O:18][CH2:19][C:20]1[C:25]([Br:26])=[CH:24][C:23]([F:27])=[CH:22][C:21]=1Br)(=[O:17])[CH3:16].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.C([O-])([O-])=O.[Cs+].[Cs+]>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:15]([O:18][CH2:19][C:20]1[C:21]([N:5]2[C:6](=[O:14])[C:7]3[S:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:1]=4[C:2]=3[CH2:3][CH2:4]2)=[CH:22][C:23]([F:27])=[CH:24][C:25]=1[Br:26])(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2685283,4-dihydro[1]benzothieno[2,3-c]pyridin-1(2h)-oneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 670165932,6-Dibromo-4-fluorobenzyl acetate

Product 1

HCID 58043775HCID 58043775, compoundYield 33%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of 329f (700 mg, 3.4 mmol), 197c (3.35 g, 10.2 mmol), XantPhos (200 mg, 0.34 mmol), Pd2(dba)3 (316 mg, 0.34 mmol) and Cs2CO3 (2.25 g, 6.8 mmol) in dioxane (50 mL) was heated at 100° C. for 15 h under argon atmosphere. It was then filtered and evaporated in vacuo. The residue was purified by column chromatography eluting with 1:3 ethyl acetate/petroleum ether to give 329g as a white solid (500 mg, 33%). MS: [M+H]+ 448.

Workup

  1. filtrationIt was then filtered
  2. customevaporated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluting with 1:3 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-fb2a9b57dbf84fb0adb5360fff733726
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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