Dimethylformamide → HCID 11640901, compound

HRID 1880465Notes

Reaction equation

HRID 1880465 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[O:8][CH2:7][C:6]2=1.[H-].[Na+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN([CH:33]=[O:34])C>>[CH2:22]([O:34][C:33]1[CH:11]=[CH:6][C:5]([CH2:13][N:12]2[C:11]3[C:10]4[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=4[O:8][CH2:7][C:6]=3[C:5]3[C:13]2=[CH:14][CH:15]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:4][CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 619571HCID 619571, compound

Product 1

HCID 11640901HCID 11640901, compound

Procedure

To a mixture of 8-methoxy-6,11-dihydro-5-oxa-11-aza-benzo[a]fluorene (100 mg, 0.398 mmoL) in DMF (2 mL) was added NaH (60%, 24 mg, 0.598 mmoL) at 0° C. After 10 minutes, benzyl chloride (139 mg, 0.598 mmoL) was added dropwise into the reaction mixture at 0° C. The reaction mixture was slowly warmed to room temperature over 2 hours. The reaction mixture was then partitioned between EtOAc and saturated NH4Cl. The aqueous phase was extracted two times with EtOAc. The organic layers from the two extractions were combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The oil was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent) to yield the title compound as a pale solid.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and saturated NH4Cl
  2. extractionThe aqueous phase was extracted two times with EtOAc
  3. extractionThe organic layers from the two extractions
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe oil was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent)

Sources & evidence

ORD record
ord-db4231aa55fc4f5482b6c7416c4866ea
Source dataset
uspto-grants-2012_11
Patent number
US08318766B2

Reaction notes

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