Sodium hydride → 1-Biphenyl-2-ylmethyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445930Notes

Reaction equation

HRID 1445930 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.[C:15]1([C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH2:23]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:21]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][N:13]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([O:4][CH3:3])[C:10]=2[CH:11]=[C:12]1[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 534128814-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 591703691-Biphenyl-2-ylmethyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

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 2-phenylbenzyl bromide (0.40 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 25% EtOAc in hexanes) gave product 4 as a yellow foam. Yield: 375 mg (66%).

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-3901c31860ac46f39fb707e2731cdcc2
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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