Cesium carbonate → 5-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-2-methyl-8-(5-phenylpyridin-2-ylmethoxy)-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

HRID 1034262Notes

Reaction equation

HRID 1034262 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([OH:16])=[C:11]4[S:17][CH:18]([CH3:20])[CH2:19][C:9]([C:10]=34)=[C:8]2[CH2:21][CH2:22][OH:23])=[CH:4][CH:3]=1.[C:26]1([C:32]2[CH:33]=[CH:34][C:35]([CH2:38]Cl)=[N:36][CH:37]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.CCOC(C)=O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH2:38][C:35]4[CH:34]=[CH:33][C:32]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)=[CH:37][N:36]=4)=[C:11]4[S:17][CH:18]([CH3:20])[CH2:19][C:9]([C:10]=34)=[C:8]2[CH2:21][CH2:22][OH:23])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 146503502-(Chloromethyl)-5-phenylpyridineHCID 190236785-(4-Chlorobenzyl)-8-hydroxy-4-(2-hydroxyethyl)-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

Product 1

HCID 190236845-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-2-methyl-8-(5-phenylpyridin-2-ylmethoxy)-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of product from Step 5 (150 mg, 0.39 mmol), 5-phenyl-2-picolyl chloride (95 mg, 0.47 mmol) and Cs2CO3 (152 mg, 0.47 mmol) in CH3CN (5 mL) was stirred at r.t. for 20 hours, then at 60° C. for 1.5 hours. The mixture was diluted with EtOAc (25 mL), washed 3× with H2O, dried over Na2SO4, and evaporated. The residue was chromatographed on silica gel, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as an oil which solidified.

Workup

  1. waitat 60° C. for 1.5 hours
  2. washwashed 3× with H2O
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a 1:1 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-e976339517814ab8ae85304486fe4cf3
Source dataset
uspto-grants-1994_05
Patent number
US05314898

Reaction notes

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