Sodium hydride → HCID 69202343, compound

HRID 2252253Notes

Reaction equation

HRID 2252253 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[C:26]2[C:12]([CH2:13][C:14]3[C:18]([C:19]4[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=4)=[N:17][NH:16][C:15]=32)=[CH:11][C:10]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:27]=[C:26]2[C:12]([CH2:13][C:14]3[C:18]([C:19]4[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=4)=[N:17][N:16]([CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])[C:15]=32)=[CH:11][C:10]=1[O:28][CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 69201142HCID 69201142, compound

Product 1

HCID 69202343HCID 69202343, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of Example 267D (11.66 g, 26.1 mmol) and DMF (500 mL) in ice bath was added 95% NaH (0.69 g, 27.41 mmol). The mixture was stirred at room temperature for 0.5 hour and then cooled at 0° C. 2-(trimethylsilyl)ethoxymethyl chloride (4.85 mL, 27.41 mmol) was added to the mixture. After 0.5 hour, the ice bath was removed. The reaction was run at room temperature for another hour, and then poured into water. Ethyl acetate (200 mL×3) was used to extract the product. The organic solution was dried with MgSO4, concentrated, and purified by flash chromatography to give the desired product (10.84 g 72%). MS (DCI/NH3) m/z 577 (M+H)+.

Workup

  1. temperaturecooled at 0° C
  2. waitAfter 0.5 hour
  3. customthe ice bath was removed
  4. waitThe reaction was run at room temperature for another hour
  5. additionpoured into water
  6. extractionto extract the product
  7. dry with materialThe organic solution was dried with MgSO4
  8. concentrationconcentrated
  9. custompurified by flash chromatography

Sources & evidence

ORD record
ord-0b2ddffdccdb4323bdaa79bd273bba51
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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