Sodium cyanoborohydride → Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate

HRID 1034259Notes

Reaction equation

HRID 1034259 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:22])[C:20](=O)[C:9]([C:10]=34)=[C:8]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>ClCCCl.C(Cl)Cl.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:22])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 19023688Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-3-oxo-2H-thiopyrano[4,3,2-cd]indole-4-acetate

Product 1

HCID 19023676Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of product from Step 2 (886 mg) in 1,2-dichloroethane (16 mL) there was added ZnI2 (960 mg) and NaCNBH3 (440 mg). The mixture was heated to 60° for 1 hour, cooled, diluted with CH2Cl2, washed 3× with H2O, dried over Na2SO4, filtered and evaporated to afford the title product as an oil which slowly solidified. It was used as such in the next step.

Workup

  1. temperatureThe mixture was heated to 60° for 1 hour
  2. temperaturecooled
  3. washwashed 3× with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9412861b86ad4714af60a2f5c3b21bf8
Source dataset
uspto-grants-1994_05
Patent number
US05314898

Reaction notes

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