Sodium Hydroxide → HCID 12968336, compound

HRID 2306027Notes

Reaction equation

HRID 2306027 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([C:11]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[NH:13]2)=[CH:9][CH:8]=1.CN(C1C=CC=CN=1)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][S:2]([NH:6][C:7]1[N:15]=[C:14]2[C:10]([C:11]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:12]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[NH:13]2)=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chloride2×HCID 9926492HCID 9926492, compound

Product 1

HCID 12968336HCID 12968336, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonyl chloride (5 ml, 0.07 mmol) was added dropwise to 6-amino-3-(4-pyridyl)-2-(4-fluorophenyl)-7-aza-indole (17) (20 mg, 0.066 mmol), dimethylamino pyridine (1 mg, 0.007 mmol), and chloroform (3 mL). After 24 h at 23° C., an additional 4 equivalents of methanesulfonyl chloride was added. After 4 h at 23° C., NaOH (10N, 3 mL) was added. After 3 h, the mixture was extracted with ethyl acetate (50 mL), washed with water (3×15 mL), and dried (Na2SO4). After concentration in vacuo, the residue was purified by application of preparative plate chromatography (two 2 mm silica gel plates, ethyl acetate) to afford 6-(methylsulfonyl amino)-3-(4-pyridyl)-2-(4-fluorophenyl)-7-aza-indole (56): Mass Spectrum (CI) 383 (MH+).

Workup

  1. waitAfter 4 h at 23° C.
  2. waitAfter 3 h
  3. extractionthe mixture was extracted with ethyl acetate (50 mL)
  4. washwashed with water (3×15 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationAfter concentration in vacuo
  7. customthe residue was purified by application of preparative plate chromatography (two 2 mm silica gel plates, ethyl acetate)

Sources & evidence

ORD record
ord-6cc104342dbb4fa7b9918ed937af0e83
Source dataset
uspto-grants-2002_08
Patent number
US06440973B1

Reaction notes

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