1-Iodooctane → HCID 68546473, compound

HRID 1445933Notes

Reaction equation

HRID 1445933 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]2[CH:11]=[C:12]([CH3:14])[NH:13][C:9]=2[CH:8]=[CH:7][N:6]=1.I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:3][O:4][C:5]1[C:10]2[CH:11]=[C:12]([CH3:14])[N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 534128814-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 68546473HCID 68546473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of NaH (98 mg, 2.5 mmol, 60% in mineral oil) in THF (10 mL), 4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine 3 (280 mg, 1.72 mmol) in THF (3 mL) was added. The mixture was stirred at room temperature for 30 min, and then 1-iodooctane (0.41 mL, 2.2 mmol) was added, stirring was continued for 18 h. The reaction mixture was quenched with saturated NH4Cl (20 mL), extracted with EtOAc (3×40 mL). The combined organic extracts were washed with water (40 mL), brine (40 mL), dried over Na2SO4 and evaporated. Flash chromatography of the residue over silica gel, using 10% EtOAc in hexanes to 20% EtOAc in hexanes) gave product 8 as a yellow oil. Yield: 231 mg (49%).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 18 h
  4. customThe reaction mixture was quenched with saturated NH4Cl (20 mL)
  5. extractionextracted with EtOAc (3×40 mL)
  6. washThe combined organic extracts were washed with water (40 mL), brine (40 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-377ebadd0b9349958c65099565cf08e6
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

Loading…