Cesium fluoride → HCID 5276060, compound

HRID 1788475Notes

Reaction equation

HRID 1788475 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:24]3[N:28]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[C:27]4[CH:35]=[CH:36][C:37]([C:39]([OH:41])=[O:40])=[CH:38][C:26]=4[N:25]=3)[CH:14]=2)[N:9]=1.[Cl:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.[F-].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:42][C:43]1[CH:48]=[CH:47][C:46]([C:2]2[C:3]([C:8]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:24]5[N:28]([CH:29]6[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]6)[C:27]6[CH:35]=[CH:36][C:37]([C:39]([OH:41])=[O:40])=[CH:38][C:26]=6[N:25]=5)[CH:14]=4)[N:9]=3)=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 742994-Chlorophenylboronic acidHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 5276044HCID 5276044, compound

Product 1

HCID 5276060HCID 5276060, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

Compound 424 (50 mg, 0.083 mmol), 4-chlorophenylboronic acid (20 mg, 0.125 mmol), and CsF (143 mg, 0.94 mmol) were added to degassed dioxane (6 mL). A solution of 2-(dicyclohexylphosphino)biphenyl (5 mg, 0.0125 mmol) and palladium acetate (2 mg, 0.0083 mmol) in degassed dioxane (3 mL) was added to the reaction solution. The reaction was then refluxed under argon for 3 hours. The reaction was then evaporated to dryness and purified via HPLC resulting in the title compound (4 mg, 10% yield).

Workup

  1. customto degassed dioxane (6 mL)
  2. temperatureThe reaction was then refluxed under argon for 3 hours
  3. customThe reaction was then evaporated to dryness
  4. custompurified via HPLC

Sources & evidence

ORD record
ord-c0877fc4f7d040d7b6c35f3309892e7a
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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