Tributylvinyltin → HCID 68089334, compound

HRID 2370257Notes

Reaction equation

HRID 2370257 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[O:13])[CH2:9][C:10]=2[CH:11]=1.[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC>C1(C)C=CC=CC=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>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]([N:8]2[CH2:7][CH2:6][C:5]3[N:4]=[CH:3][C:2]([CH:21]=[CH2:22])=[CH:11][C:10]=3[CH2:9]2)=[O:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 68089407HCID 68089407, compound

Product 1

HCID 68089334HCID 68089334, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

(3-Bromo-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)(4-fluorophenyl)methanone (150 mg, 0.4 mmol; prepared as described above), tributyl(vinyl)tin (185 mg, 0.6 mmol) and Pd(PPh3)4 (58 mg, 0.05 mmol) were combined in toluene (12 mL) and heated at 120° C. for 1 h. The reaction mixture was cooled to RT, filtered through celite, adsorbed onto silica gel, and eluted with CH2Cl2:MeOH (9:1) to give 104 mg (82%) of (4-fluorophenyl)(3-vinyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone. LC-MS (M+H)=283.1.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered through celite
  3. washeluted with CH2Cl2:MeOH (9:1)

Sources & evidence

ORD record
ord-59013326211f4dc19123660eb4381c5c
Source dataset
uspto-grants-2014_04
Patent number
US08710074B2

Reaction notes

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