Dichloromethane → methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-6,7,8,9-tetrahydropyrido[3,2-b]indolizin-5-yl)acetate

HRID 1036634Notes

Reaction equation

HRID 1036634 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH:20]=[CH:19][C:18]3[N:14]([C:15]4[N:29]=[CH:28][CH:27]=[CH:26][C:16]=4[C:17]=3[CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:20][CH2:19][C:18]3[N:14]([C:15]4[N:29]=[CH:28][CH:27]=[CH:26][C:16]=4[C:17]=3[CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86655916methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate

Product 1

HCID 86655917methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-6,7,8,9-tetrahydropyrido[3,2-b]indolizin-5-yl)acetateYield 101%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl ((8R)-8-{[(4-fluorophenyl)sulfonyl]amino}-8,9-dihydropyrido[3,2-b]indolizin-5-yl)acetate (0.46 g, 1.1 mmol) in ethyl acetate (20 mL) was added under nitrogen Pd—C 10% (0.02 g, 0.19 mmol, 0.17 equiv.). After a period of 1 h under 1 atmosphere of H2, DCM was added to the reaction mixture which in turn was filtered over a micro filter and the solvents were evaporated to afford 464 mg of the title compound.

Workup

  1. filtrationwas filtered over
  2. filtrationa micro filter
  3. customthe solvents were evaporated

Sources & evidence

ORD record
ord-b274faf302fd4292a1f1729c7c341794
Source dataset
uspto-grants-2013_10
Patent number
US08546422B2

Reaction notes

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