Cesium fluoride → 2-[2-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-pyrazine

HRID 2218717Notes

Reaction equation

[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3B(O)O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1.[F-].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a 1-dram vial, mix 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylboronic acid (100 mg, 0.307 mmol), chloropyrazine (69 mg, 0.460 mmol), cesium fluoride (94 mg, 0.614 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (1:1 complex with CH2C2, 25 mg, 0.031 mmol) in dioxane (2 mL). Heat to 85° C. for 72 h, then remove solvent under nitrogen. Take up the resulting residue in H2O (1 mL) and CH2Cl2 (1 mL) and load onto a Varian ChemElut CE1005 solid-phase extraction cartridge. Elute, collect, and concentrate 15 mL CH2Cl2 to obtain crude product. Purify by mass-guided reverse-phase HPLC to obtain 2.3 mg (2%) of the title compound. MS (ES) 361 (M+H); HPLC shows 93% purity.

Workup

extractionCH2Cl2 (1 mL) and load onto a Varian ChemElut CE1005 solid-phase extraction cartridge
washElute
customcollect
concentrationconcentrate 15 mL CH2Cl2
customto obtain crude product
customPurify by mass-guided reverse-phase HPLC

Sources & evidence

ORD record: ord-6d69a0b2c2b640da98eb0cd77ff6a715
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07411072B2

Reaction notes

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