Tributylstannane → 1,1,8-Triethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 901059Notes

Reaction equation

HRID 901059 reaction equation
Cl[CH2:2][CH2:3][C:4]1([CH2:19][CH3:20])[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[CH2:7][CH2:6][O:5]1)=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:17][CH3:18].CC(N=NC(C#N)(C)C)(C#N)C.[SnH](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[CH2:19]([C:4]1([CH2:3][CH3:2])[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[CH2:7][CH2:6][O:5]1)=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:17][CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 219075721-(2-Chloroethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

Product 1

HCID 219075761,1,8-Triethyl-1,3,4,9-tetrahydropyrano[3,4-b]indoleYield 62.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of compound 4 (103 mg, 0.35 mmol), AIBN (11 mg, 0.07 mmol, 0.2 eq), and toluene (3 mL) at room temperature under argon, HSnBu3 (380 μL, 1.41 mmol, 4.0 eq) was added in a dropwise manner. The resulting mixture was stirred overnight at 110° C. and concentrated. The residue was diluted with hexane and extracted three times with acetonitrile. The acetonitrile layers were combined, concentrated, and purified by column chromatography using 3:97:EtOAc:Hexane to give an off-white solid (56 mg, 62%): mp 133-134° C. 1HNMR (CDCl3, δ TMS): 0.88 (t, 6H), 1.37 (t, 3H), 1.87 (q, 4H), 2.78 (t, 2H), 2.86 (q, 2H), 4.02 (t, 2H), 7.01-7.38 (m, 3H, Ar—H), 7.46 (br, 1H, NH). MS−: m/z 256 ([M−H]−). Anal. (C17H23NO): C, H, N.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with hexane
  3. extractionextracted three times with acetonitrile
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-2197863d32bf4ed2872b4e8b49580f78
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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