Triethylamine → HCID 21984387, compound

HRID 244830Notes

Reaction equation

HRID 244830 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[CH:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1.[CH2:20](N(CC)CC)[CH3:21].C([B-](F)(F)F)=C.[K+]>C(O)CC.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]>[CH2:16]([N:15]1[C:5]2[C:4]3[CH:3]=[C:2]([CH:20]=[CH2:21])[CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:12])[C:6]=2[N:13]=[CH:14]1)[CH:17]([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 21984387HCID 21984387, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10311-PropanolSolvent

Procedure

8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine (22.0 g, 68.9 mmol), triethylamine (19.20 mL, 137.8 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (1.00 g, 1.37 mmol), and potassium vinyltrifluoroborate (10.15 g, 75.81 mmol) were dissolved in n-propanol (20 mL/g). The amber colored solution was heated at reflux temperature for 18 hours and then cooled to ambient temperature. The reaction was concentrated under reduced pressure. The resulting solid was slurried in 1% aqueous sodium carbonate and a fine powder was collected by filtration. The powder was sequentially washed with acetonitrile (5 mL/g) and 10% sodium hydroxide (500 mL). A final purification using a HORIZON HPFC system (silica cartridge, eluting with 4% methanol/dichloromethane) provided 10 g of 1-isobutyl-8-vinyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, MS (APCI) m/z 267 (M+H)+.

Workup

  1. temperatureThe amber colored solution was heated
  2. temperatureat reflux temperature for 18 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. filtrationa fine powder was collected by filtration
  5. washThe powder was sequentially washed with acetonitrile (5 mL/g) and 10% sodium hydroxide (500 mL)
  6. customA final purification
  7. washa HORIZON HPFC system (silica cartridge, eluting with 4% methanol/dichloromethane)

Sources & evidence

ORD record
ord-43b79e4f8fe04c5c84af18d5b3f4b772
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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