Diethyl Ether → HCID 44199845, compound

HRID 1677489Notes

Reaction equation

HRID 1677489 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH2:11]([O:18][CH:19]1[CH2:24][CH2:23][C:22]([CH3:28])([C:25](Cl)=[O:26])[CH2:21][CH2:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al](Cl)(CC)CC.CCOCC>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:11]([O:18][CH:19]1[CH2:24][CH2:23][C:22]([C:25]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Br:1])[N:3]=3)[NH:8][CH:9]=2)=[O:26])([CH3:28])[CH2:21][CH2:20]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7277Diethylaluminum chlorideHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazineHCID 59540922HCID 59540922, compound

Product 1

HCID 44199845HCID 44199845, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (531 mg, 2.68 mmol) and 4-benzyloxy-1-methyl-cyclohexanecarbonyl chloride (2.15 g, 8.05 mmol) in anhydrous Toluene (16 ml) was treated with Et2AlCl (1M in Hexanes, 5.36 ml, 5.36 mmol), dropwise. The reaction mixture was stirred at 90° C. for 16 hours. The reaction mixture was cooled to room temperature, quenched with sat. NaHCO3, and extracted with ethyl acetate (3×). The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a dark brown oil. Silica gel chromatography using 0-50% Et2O in DCM as eluant provided 205 mg (18%) of (4-benzyloxy-1-methyl-cyclohexyl)-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-methanone as a pale yellow solid. M−H=426.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with sat. NaHCO3
  3. extractionextracted with ethyl acetate (3×)
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving a dark brown oil

Sources & evidence

ORD record
ord-3038654809a94f5db46900bd3de23878
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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