Sodium hydride → HCID 67044778, compound

HRID 2367092Notes

Reaction equation

HRID 2367092 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl.[Cl-].[NH4+]>O1CCCC1.CCOCC>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 67044778HCID 67044778, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (0.27 g, 6.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added 5-bromoindole (1.0 g, 5.1 mmol). The reaction was stirred for 30 min at room temperature, then cooled to 0° C. and 2-(trimethylsilyl)ethoxymethyl chloride (1.0 mL, 5.6 mmol) was added. The solution was stirred for 2 h at room temperature. The reaction mixture was poured into saturated aqueous ammonium chloride solution and diluted with ether. The layers were separated and the aqueous layer was extracted (2×100 mL ether). The combined organic layers were washed with brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 20:1 hexanes/ethyl acetate) gave 1.1 g (66%) of 5-bromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indole. 1H NMR (400 MHz, CDCl3): 7.81 (d, 1H), 7.42 (d, 1H), 7.38 (dd, 1H), 7.23 (d, 1H), 6.52 (dd, 1H), 5.51 (s, 2H), 3.60 (m, 2H), 0.93 (m, 2H), 0.00 (s, 9H); MS (EI) for C14H20NOSiBr: 209 (M−OCH2CH2Si(CH3)3).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe solution was stirred for 2 h at room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted (2×100 mL ether)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c558830c3983470190b3bfe3344ef754
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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