Sodium hydride → HCID 11713695, compound

HRID 2040472Notes

Reaction equation

HRID 2040472 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=4[C:21]=3[O:22][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:31][C:32]1[CH:45]=[CH:44][C:35]([O:36][CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:34][CH:33]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[C:13]3[N:14]([CH2:31][C:32]4[CH:45]=[CH:44][C:35]([O:36][CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:34][CH:33]=4)[C:15]4[CH:16]=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=4[C:21]=3[O:22][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11515692HCID 11515692, compoundHCID 124936922-[4-(Chloromethyl)phenoxy]-N,N-diethylethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 11713695HCID 11713695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 7-benzyloxy-3-methoxy-10H-benzo[4,5]furo[3,2-b]indole (102 mg, 0.297 mmol) in DMF (5 mL) was added NaH (37 mg, 60% in mineral oil, 3.0 eq.) followed by [2-(4-chloromethyl-phenoxy)-ethyl]-diethyl-amine hydrochloride salt (99 mg, 0.356 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes, warmed to 25° C., and quenched by NH4Cl (solid). EtOAc and water were then added to the mixture. The reaction mixture was then partitioned between EtOAc and water. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield crude material. The crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1) to yield the title compound as a brown solid.

Workup

  1. temperaturewarmed to 25° C.
  2. customquenched by NH4Cl (solid)
  3. additionEtOAc and water were then added to the mixture
  4. customThe reaction mixture was then partitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted three times with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield crude material
  11. customThe crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1)

Sources & evidence

ORD record
ord-0dc2de93c9d24a9199a7a0e49f22dce8
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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