Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate

HRID 1036633Notes

Reaction equation

HRID 1036633 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:28][CH:29]=O)[CH2:13][N:14]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH:28]=[CH:29][C:15]3[N:14]([C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:17]=4[C:16]=3[CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86655915Methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

Product 1

HCID 86655916methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetateYield 70.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl]amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (0.69 g, 1.6 mmol) in toluene (50 mL) was added PPTS (0.41 g, 1.6 mmol, 1.2 equiv.). After a period of 10 h at 90° C., the reaction mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate) to give 469 mg of the title compound.

Workup

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-e39ee06a536a4ac7a2e2f9cf3dfeb2c7
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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