Cesium fluoride → HCID 69507779, compound

HRID 1375677Notes

Reaction equation

HRID 1375677 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1.[F-].[Cs+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([Sn](CCCC)(CCCC)[CH2:39][CH2:40][CH2:41][OH:42])CCC>O1CCOCC1>[NH2:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](/[CH:39]=[CH:40]/[CH2:41][OH:42])[CH:8]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 6010493-(Tributylstannyl)-1-propanolHCID 69507735HCID 69507735, compound

Product 1

HCID 69507779HCID 69507779, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a dioxane (4 mL) solution of compound from Example 21C (710 mg, 2.3 mmol) was added Pd3(dba)2-CHCl3 (71 mg, 0.07 mmol, 3% equiv.) and CsF (760 mg, 5.1 mmol, 2.2 equiv.) under N2. P(tBu)3 (10% in hexanes, 0.42 mL, 0.14 mmol, 12% equiv) and 3-tributylstannyl-1-propanol (1.1 g, 3.2 mmol, 1.1 equiv.) were added sequentially. The mixture was flushed with N2 for 2 min and then heated to 100° C. in a sealed culture tube. The mixture was purified by flash column chromatography (50% ethyl acetate in hexanes) to provide the titled compound (150 mg, 22%).

Workup

  1. customThe mixture was flushed with N2 for 2 min
  2. customThe mixture was purified by flash column chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-38283b4157b64fccb394ca4e8b37c109
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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