Sodium Hydroxide → HCID 118022968, compound

HRID 1503352Notes

Reaction equation

HRID 1503352 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][CH:16]=O)[CH:13]=2)[N:8]([CH3:18])[CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][N:25]=C(S(C)(=O)=O)[N:23]=1.[OH-].[Na+]>C1COCC1.CN(C=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][N:25]=[C:16]([NH:15][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]([CH3:18])[CH:7]=[C:6]3[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[N:23]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 111482324-Chloro-2-(methylsulfonyl)pyrimidineHCID 118023783HCID 118023783, compound

Product 1

HCID 118022968HCID 118022968, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-isobutyryl-1-methyl-1H-indol-5-yl)formamide (450 mg, 1.84 mmol) in anhydrous THF (3 mL) and anhydrous DMF (3 mL) was added 60% NaH (228 mg, 5.52 mmol) at 0° C. After being stirred for 30 min at room temperature, it was cooled to 0° C. To this, was added 4-chloro-2-(methylsulfonyl)pyrimidine (466 mg, 2.43 mmol) and then stirred for 2 hours. Quenching the reaction by addition of ice and 2N solution of sodium hydroxide (2 mL) resulted precipitation of brown solids. Additional 20 mL of water was added to complete of solid formation. The resulted solids were collected by filtration, rinsed with water and the dried in vacuo to provide the desired intermediate 5 as a brown solid (542 mg, 89%); MS (ESI) m/z 329 [M+H]+.

Workup

  1. temperatureit was cooled to 0° C
  2. stirringstirred for 2 hours
  3. customQuenching
  4. customthe reaction
  5. customresulted
  6. customprecipitation of brown solids
  7. additionAdditional 20 mL of water was added to complete of solid formation
  8. filtrationThe resulted solids were collected by filtration
  9. washrinsed with water
  10. customthe dried in vacuo

Sources & evidence

ORD record
ord-858668919c5e47e1984e41dc72999d34
Source dataset
uspto-grants-2015_12
Patent number
US09212178B2

Reaction notes

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