2-Bromopropane → HCID 22477357, compound

HRID 549086Notes

Reaction equation

HRID 549086 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([C:18]3[N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[CH:19]=3)=[CH:13][N:14]2[CH3:17])=[CH:10][C:9]=1[O:37][CH3:38].Br[CH:40]([CH3:42])[CH3:41]>CN(C)C=O.O>[CH:40]([O:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([C:18]3[N:26]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[C:21]4=[N:22][CH:23]=[CH:24][CH:25]=[C:20]4[CH:19]=3)=[CH:13][N:14]2[CH3:17])=[CH:10][C:9]=1[O:37][CH3:38])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 63582-Bromopropane2×HCID 11430Potassium Carbonate2×HCID 22477326HCID 22477326, compound

Product 1

HCID 22477357HCID 22477357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (70 mg) was added to a solution of 2-(6-hydroxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [112 mg, Reference Example 83] in dry dimethylformamide (5 mL) under an argon atmosphere at ambient temperature. The mixture was allowed to stir for 10 minutes then treated with 2-bromopropane (66 μl) and heated at 70° C. for 3 hours. Additional portions of potassium carbonate (70 mg) and 2-bromopropane (66 μl) were then added and the mixture was stirred and heated at 70° C. for 4 hours. The cooled reaction mixture was poured in water (20 mL) and extracted three times with ethyl acetate (40 mL). The combined organic phases were washed with brine (20 mL), then dried over magnesium sulfate and then evaporated. The brown residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (3:2, v/v) to give the title compound (56 mg) as an off-white foam. TLC: RF=0.47 (cyclohexane/ethyl acetate, 1/1). MS: CI (NH3); m/z=490 MH+.

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated at 70° C. for 4 hours
  3. customThe cooled reaction mixture
  4. extractionextracted three times with ethyl acetate (40 mL)
  5. washThe combined organic phases were washed with brine (20 mL)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionThe brown residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (3:2, v/v)

Sources & evidence

ORD record
ord-f65794dcda574a459269771825ab6226
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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