Tributylvinyltin → (2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine

HRID 1170081Notes

Reaction equation

HRID 1170081 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[CH:22]([Sn](CCCC)(CCCC)CCCC)=[CH2:23]>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>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH:22]=[CH2:23])[N:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Product 1

HCID 44218150(2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (1000 mg, 2.92 mmol) was dissolved in 30 mL toluene. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Vinyltributyltin (952 mg, 3.00 mmol) and tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.058 mmol) were added. The reaction mixture was refluxed overnight and evaporated. The residue was poured into 50 mL acetonitrile and extracted three times with heptane (50 mL each) to remove the tin products. The acetonitrile phase was dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine was obtained as a light yellow gum (544 mg, 64%), MS: m/e=291.3 (M+H+).

Workup

  1. customThe reaction mixture was evacuated
  2. customto remove oxygen
  3. temperatureThe reaction mixture was refluxed overnight
  4. customevaporated
  5. additionThe residue was poured into 50 mL acetonitrile
  6. extractionextracted three times with heptane (50 mL each)
  7. customto remove the tin products
  8. dry with materialThe acetonitrile phase was dried with sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-df8ac459ebca4fdd9459967ac8475861
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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