1-Methyl-5-(tri-n-butylstannyl)imidazole → HCID 52934103, compound

HRID 2366941Notes

Reaction equation

HRID 2366941 reaction equation
[CH3:1][N:2]1[C:6]([Sn](CCCC)(CCCC)CCCC)=[CH:5][N:4]=[CH:3]1.[C:20]([N:23]1[C:32]2[C:27](=[CH:28][C:29](Br)=[CH:30][CH:31]=2)[C@H:26]([NH:34][C:35](=[O:40])[O:36][CH:37]([CH3:39])[CH3:38])[CH2:25][C@@H:24]1[CH3:41])(=[O:22])[CH3:21]>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.CCOC(C)=O.CCCCCC>[CH3:39][CH:37]([O:36][C:35](=[O:40])[NH:34][C@H:26]1[C:27]2[C:32](=[CH:31][CH:30]=[C:29]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)[CH:28]=2)[N:23]([C:20](=[O:22])[CH3:21])[C@@H:24]([CH3:41])[CH2:25]1)[CH3:38]

Participants

5

Reactant 2

HCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 52934103HCID 52934103, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-methyl-5-(tributylstannyl)-1H-imidazole (200 mg, 0.54 mmol), 1-methylethyl [(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (199 mg, 0.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol) in dry, degassed DMF (5 mL) was stirred at 140° C. under nitrogen for 16 h then was cooled to room temperature and diluted with AcOEt (20 mL). The solution was washed with water (×2) then brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(1-methyl-1H-imidazol-5-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (27 mg, 0.073 mmol, 13%) as a colourless solid after trituration with AcOEt/hexane. LCMS (method G): Retention time 0.59 min, [M+H]+=402.1

Workup

  1. customfor a preparation
  2. customin dry
  3. customdegassed DMF (5 mL)
  4. temperaturethen was cooled to room temperature
  5. additiondiluted with AcOEt (20 mL)
  6. washThe solution was washed with water (×2)
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM)

Sources & evidence

ORD record
ord-3f3ab2351f2f46c3aa5a91feedb649c4
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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