HCID 19592337, compound → HCID 19592649, compound

HRID 613539Notes

Reaction equation

HRID 613539 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:29]2[C:24](=[C:25]([NH:30][C:31](=[O:40])[C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[C:41](=[O:46])N(OC)C)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[Si:1]([O:18][CH2:19][C:20]1[C:29]2[C:24](=[C:25]([NH:30][C:31](=[O:40])[C:32]3[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:39])[CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[CH:41]=[O:46])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 19592337HCID 19592337, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19592649HCID 19592649, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-52.5 °C

Procedure

To a solution of 4-(tert-butyldiphenylsilyloxymethyl)-8-(2,6-dichlorobenzoylamino)-3-(N-methoxy-N-methylcarbamoyl)quinoline (1.03 g) in tetrahydrofuran (10 ml) was dropwise added 1M solution of diisobutylaluminum hydride in tetrahydrofuran (15 ml) at -55° C., and the mixture was stirred for 50 minutes at -60 to -45° C. The mixture was quenched by saturated ammonium chloride solution and 101, aqueous solution of potassium sodium tartrate. Diethyl ether (50 ml) was added to the mixture, and the mixture was stirred for 1.5 hours at ambient temperature. The separated aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 4-(tert-butyldiphenylsilyloxymethyl)-8-(2,6-dichlorobenzoylamino)-3-formylquinoline (809 mg).

Workup

  1. customat -55° C.
  2. customThe mixture was quenched by saturated ammonium chloride solution and 101, aqueous solution of potassium sodium tartrate
  3. additionDiethyl ether (50 ml) was added to the mixture
  4. stirringthe mixture was stirred for 1.5 hours at ambient temperature
  5. extractionThe separated aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-44002f6443d04d2aa920f04ce9b91e0e
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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