Hexane → HCID 11072013, compound

HRID 890998Notes

Reaction equation

HRID 890998 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CCCCCC.[CH2:26]([O:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]([C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43]([S:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)(=[O:52])=[O:51])[CH:42]=2)=[C:37](Br)[C:36]1=[O:60])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH2:26]([O:33][CH2:34][N:35]1[C:36](=[O:60])[C:37]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[C:38]([C:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43]([S:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)(=[O:52])=[O:51])[CH:42]=2)[C:39]1=[O:40])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11017101HCID 11017101, compound

Product 1

HCID 11072013HCID 11072013, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a solution, held at −15° C., of 7-azaindole (1.542 mmol), dissolved in 10 ml of dry toluene, there is added, dropwise, a 1M solution of LiHMDS in hexane (1.78 mmol). After stirring for 1 hour at −15° C., a solution of the compound of Step B (0.637 mmol), dissolved in 10 ml of dry toluene, is added, dropwise, at −20° C. After 24 hours at ambient temperature, the reaction mixture is hydrolysed with saturated aqueous ammonium chloride solution and the pH is then adjusted to 7. The mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered. After purifying by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2), the expected product is isolated.

Workup

  1. additionthere is added
  2. additionis added
  3. customat −20° C
  4. waitAfter 24 hours at ambient temperature
  5. extractionThe mixture is extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customAfter purifying by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-08bba9630e9742988e9e9696ea3d3d21
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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