Sodium hydride → HCID 23249079, compound

HRID 2215768Notes

Reaction equation

HRID 2215768 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[H-].[Na+]>CN(C=O)C>[C:20]([Si:17]([CH3:19])([CH3:18])[O:16][CH2:15][CH2:14][CH2:13][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH:7]=[CH:8]1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766596-Methoxy-1H-indoleHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 23249079HCID 23249079, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methoxyindole (10.0 g, 67.9 mmol), and (3-bromo-propoxy)-tert-butyl-dimethylsilane (18.0 g, 71.3 mmol) in DMF (300 mL) was added NaH (0.353 g, 8.82 mmol) as a 60% oil dispersion. The reaction was stirred for 2 h, quenched with saturated aq NaHCO3, diluted with EtOAc (400 mL), washed with saturated aq NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to a transparent oil. The oil was purified by filtration through a plug of silica gel (85% hexane/EtOAc) to give (22.1 g, 100%) of the title compound as a transparent oil. 1H NMR (DMSO-d6) 7.38 (d, J=8.4 Hz, 1H), 7.15 (d, J=3.2 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.65 (dd, J=2.4, 8.4 Hz, 1H), 6.32 (d, J=3.2 Hz, 1H) 4.16 (t, J=6.4 Hz, 2H), 3.77 (s, 3H), 3.53 (t, J=6 Hz, 2H), 1.90 (apparent quintet, J=6.8 Hz, 2H), 0.87 (s, 9H), 0.01 (s, 6H). MS (electrospray, m/z) 320 (M++1).

Workup

  1. customquenched with saturated aq NaHCO3
  2. additiondiluted with EtOAc (400 mL)
  3. washwashed with saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a transparent oil
  7. filtrationThe oil was purified by filtration through a plug of silica gel (85% hexane/EtOAc)

Sources & evidence

ORD record
ord-06c4726388be496c9f0707fcb0a3266b
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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