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

HRID 1036638Notes

Reaction equation

HRID 1036638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:31])[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>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:31])[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:6][CH:7]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86762093Methyl {1-[(2R)-2-{[(4-fluorophenyl)sulfonyl](methyl)amino}-4-oxobutyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}acetate

Product 1

HCID 86762094Methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl](methyl)amino}-8,9-dihydro-pyrido[3,2-b]indolizin-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl [1-((2R)-2-{[(4-fluorophenyl)sulfonyl](methyl)amino}-4-oxobutyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate (272 g, 589 mmol) in ethyl acetate (2.5 L) was added PPTS (326.33 g, 1299 mmol). After a period of 4 days at 65° C., the reaction mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was separated, washed with brine, 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 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. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by combiflash (10% ethyl acetate in hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-a6a59821ecf34f04b4b0fc69c3686317
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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