Tetrahydrofuran → 6-(2,2-dimethylpropyl)-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

HRID 20038Notes

Reaction equation

HRID 20038 reaction equation
[CH2:1]([Mg]Cl)[C:2]([CH3:5])([CH3:4])[CH3:3].Br[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:20])([CH3:19])[CH2:13][CH:12]2[NH2:21].O1CCCC1>[Cl-].[Zn+2].[Cl-]>[CH3:19][C:14]1([CH3:20])[CH2:13][CH:12]([NH2:21])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[CH:10]=2)[NH:15]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 673058276-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-QuinolinamineHCID 178418809HCID 178418809, compound

Product 1

HCID 673051226-(2,2-dimethylpropyl)-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To neopentylmagnesium chloride (1.65 ml, 1.65 mmol) was added zinc(II) chloride (2.19 ml, 1.10 mmol) dropwise—strong exotherm was observed. The resulting mixture stirred for 10 minutes. A solution of 6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinolin-4-amine (0.0700 g, 0.274 mmol) in tetrahydrofuran (1.37 ml, 0.274 mmol) was then added followed by palladium tetrakistriphenylphosphine (0.0317 g, 0.0274 mmol). The reaction vessel was sealed and heated to 65 deg C. The reaction mixture was stirred for 6 hours. The crude mixture was filtered through a plug of celite with EtOAc and concentrated in the presence of silica gel. The crude mixture was purified with the MPLC (100% DCM to 100% 90:10:1 DCM:MeOH:NH4OH) to provide the desired product. MS m/z: 230 (M−NH2).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated to 65 deg C
  3. stirringThe reaction mixture was stirred for 6 hours
  4. filtrationThe crude mixture was filtered through a plug of celite with EtOAc
  5. concentrationconcentrated in the presence of silica gel
  6. customThe crude mixture was purified with the MPLC (100% DCM to 100% 90:10:1 DCM:MeOH:NH4OH)

Sources & evidence

ORD record
ord-858a129732b542ffb86522463a3809ce
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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