2-Bromo-5-fluoropyridine → HCID 86637811, compound

HRID 425426Notes

Reaction equation

HRID 425426 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:20][CH2:19][CH2:18][C:17]=2[CH:21]=[O:22])=[CH:12][CH:11]=1.C[Sn](C)C.C[Sn](C)C>O1CCOCC1.C(OCC)C.[F-].[Cs+].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>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][CH2:19][CH2:18][C:17]=3[CH:21]=[O:22])=[CH:12][CH:11]=2)=[N:3][CH:4]=1

Participants

8

Reactant 3

HCID 27831712-Bromo-5-fluoropyridineHCID 6327618HexamethylditinHCID 86637810HCID 86637810, compound

Product 1

HCID 86637811HCID 86637811, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 25953Cesium fluorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Pd(PPh3)4 (230 mg, 0.20 mmol) was added to a solution of 2-bromo-5-fluoropyridine (350 mg, 2.0 mmol), 2-(4-bromophenyl)cyclopent-1-ene-1-carbaldehyde (500 mg, 2.0 mmol) and hexamethylditin (652 mg, 2.0 mmol) in degassed 1,4-dioxane (10 mL) at ambient temperature. After stirring at 110° C. for a further 3 days, the reaction mixture was diluted with diethyl ether and CsF/celite (1:1) was added. After stirring vigorously for 1 hr, reaction mixture was filtered and concentrated. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded 2-[4-(5-fluoropyridin-2-yl)phenyl]cyclopent-1-ene-1-carbaldehyde as an orange gum.

Workup

  1. additionwas added
  2. stirringAfter stirring vigorously for 1 hr
  3. customreaction mixture
  4. filtrationwas filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a9d93e4fb4c41abb8e0c1a2cf3e5417
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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