Sodium hydride → HCID 58009950, compound

HRID 1854306Notes

Reaction equation

HRID 1854306 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C.O>[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:23]([C:20]3[CH:21]=[CH:22][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 58009950HCID 58009950, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2-bromo-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 25.2 mmol, Ark Pharm) in DMF (150 mL) was cooled in an ice bath to about 0° C. and then NaH (60% dispersion in mineral oil, 1.21 g, 30.3 mmol) was added. After about 15 min, 4-tert-butylbenzene-1-sulfonyl chloride (6.46 g, 27.8 mmol) was added. The reaction was maintained between about 0-10° C. for about 2 h. Then, the reaction was diluted with water (200 mL) to give a yellow suspension. The solid was collected by vacuum filtration, while washing with additional water (100 mL), and dried in a vacuum oven at about 70° C. to give 2-bromo-5-(4-tert-butylphenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (9.05 g, 91%): LC/MS (Table 2, Method a) Rt=3.05 min; MS m/z: 394/396 (M+H)+.

Workup

  1. customto give a yellow suspension
  2. filtrationThe solid was collected by vacuum filtration
  3. washwhile washing with additional water (100 mL)
  4. customdried in a vacuum oven at about 70° C.

Sources & evidence

ORD record
ord-39f596002e0d47ffbeff7d9d00a3ea4d
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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