Cesium fluoride → HCID 57856043, compound

HRID 1715205Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F-].[Cs+].[C:10]1([CH2:16][N:17]2[CH2:21][CH:20]=[C:19](B3OC(C)(C)C(C)(C)O3)[CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]1([CH2:16][N:17]2[CH2:21][CH:20]=[C:19]([C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-bromopyrimidine (0.88 g) in dry tetrahydrofuran (30 mL) 1-(phenylmethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole (P13, 1.21 g), tetrakis(triphenylphosphine)palladium(0) (0.25 g) and cesium fluoride (2.59 g) were added at room temperature. The resulting mixture was stirred at 80° C. for 6 hours. After cooling the solvent was evaporated under reduced pressure, the residue partitioned between ether and water and the organic phase was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (eluting with DCM/MeOH from 100% to 96%) to give 0.23 g of the title compound.

Workup

temperatureAfter cooling the solvent
customwas evaporated under reduced pressure
customthe residue partitioned between ether and water
customthe organic phase was evaporated under reduced pressure
customThe crude product was purified by silica gel column chromatography (eluting with DCM/MeOH from 100% to 96%)

Sources & evidence

ORD record: ord-ab2a95a4a4464b098e8864da147adb44
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799815B2

Reaction notes

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