Iodoethane → HCID 67976988, compound

HRID 712462Notes

Reaction equation

HRID 712462 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][NH:8][CH2:9][C:2]=12.[H-].[Na+].I[CH2:13][CH3:14]>C1COCC1>[CH2:13]([N:8]1[CH2:7][C:3]2[C:2](=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:9]1)[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 15194166,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Product 1

HCID 67976988HCID 67976988, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (5.00 g) in THF was added 80% NaH (3.00 g) at rt. The reaction mixture was stirred for 30 min at room temperature, and 5.3 mL of iodoethane was added dropwise. The reaction mixture was stirred for another 5 h, then quenched with ice water, and extracted with CH2Cl2 (70 mL×5). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH) to give the title compound as a pale yellow solid (2.80 g, 45.00%), HPLC: 90.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 149.3 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 1.02 (t, J=4.8 Hz, 3H), 2.64 (m, 2H), 3.62 (s, 2H), 3.95 (s, 2H), 7.11-7.83 (m, 3H) ppm.

Workup

  1. stirringThe reaction mixture was stirred for another 5 h
  2. customquenched with ice water
  3. extractionextracted with CH2Cl2 (70 mL×5)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-280bbb7e1f084965960a8809ec5adea8
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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