Iodoethane → HCID 22179368, compound

HRID 897156Notes

Reaction equation

HRID 897156 reaction equation
[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[C:16]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:34][CH3:35]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[C:16]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH:15]=[CH:14][C:13]=3[N:12]([CH2:34][CH3:35])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22179371HCID 22179371, compound

Product 1

HCID 22179368HCID 22179368, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° mixture of 3-benzyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (EXAMPLE 1, Step II, 301 mg, 0.723 mmol) in dry DMF (5 mL) is treated with sodium hydride (60% in oil, 32 mg, 0.795 mmol), and allowed to warm to 20-25° over 1.5 hr. The mixture is then cooled (0°), treated with iodoethane (64 μL, 0.795 mmol) and allowed to slowly warm to 20-25° under nitrogen over 72 hr. The resultant mixture is diluted with ethyl acetate (50 mL) and washed with H2O (3×25 mL) and saline (25 mL). The organic layer is dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give a solid. The solid is purified via chromatography (20 g SG; ethyl acetate/heptane, 65/35) to give the indole as a solid, mp=188-191°; IR (drift) 1477, 1373, 1300, 1289, 1157, 1148, 1094, 766, 756, 738, 728, 701, 694, 645 and 621 cm−1; NMR (300 MHz, CDCl3) 8.10-8.20, 7.90-8.05, 7.65-7.75, 7.20-7.50, 4.11, 3.82, 2.85-3.05 and 1.27 δ; MS (EI) m/z 444 (M+), 326, 324, 312, 167, 154, 132, 118, 96, 91 and 64.

Workup

  1. temperatureto warm to 20-25° over 1.5 hr
  2. temperatureThe mixture is then cooled (0°)
  3. temperatureto slowly warm to 20-25° under nitrogen over 72 hr
  4. washwashed with H2O (3×25 mL) and saline (25 mL)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. customThe solid is purified via chromatography (20 g SG; ethyl acetate/heptane, 65/35)

Sources & evidence

ORD record
ord-3b0c2e46c9064b13b333519ed8beda43
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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