1H-Pyrrolo(2,3-b)pyridine → HCID 13006222, compound

HRID 891002Notes

Reaction equation

HRID 891002 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.Br[C:21]1[C:25](=[O:26])[N:24]([CH3:27])[C:23](=[O:28])[C:22]=1[C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:30]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:27][N:24]1[C:25](=[O:26])[C:21]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[C:22]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH:30]=2)[C:23]1=[O:28]

Participants

6

Reactant 4

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 9865966HCID 9865966, compound

Product 1

HCID 13006222HCID 13006222, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution, maintained at −10° C., of 7-azaindole (1.78 mmol), dissolved in 10 ml of dry toluene, there is added, dropwise, a solution of commercial LiHMDS (1M in hexane) (4.6 mmol). After stirring for 1 hour at −10° C., a solution of the product obtained in Step B (0.85 mmol), dissolved in 10 ml of dry toluene, is added dropwise at ambient temperature. After stirring for 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 aqueous sodium chloride solution and dried over magnesium sulphate. After purification by chromatography on silica gel (cyclohexane/ethyl acetate/triethylamine: 7/3/1%), the expected product is isolated.

Workup

  1. additionthere is added
  2. additionis added dropwise at ambient temperature
  3. stirringAfter stirring for 24 hours at ambient temperature
  4. extractionThe mixture is extracted with ethyl acetate
  5. washwashed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customAfter purification by chromatography on silica gel (cyclohexane/ethyl acetate/triethylamine: 7/3/1%)

Sources & evidence

ORD record
ord-f7c560ee88764e53a95a63ad71be7d78
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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