Bromine → 3,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2-chloro-4-fluorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5-Dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl ester

HRID 2102876Notes

Reaction equation

HRID 2102876 reaction equation
BrBr.[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[CH2:18][CH2:17][N:16]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:15](=[O:26])[C:14]=2[C:13]([CH3:27])=[C:12]1[C:28]1[CH:33]=[CH:32][C:31]([O:34][S:35]([CH2:38][CH2:39][C:40]([F:43])([F:42])[F:41])(=[O:37])=[O:36])=[CH:30][CH:29]=1>C(O)(=O)C.C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[CH:18]=[CH:17][N:16]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[C:15](=[O:26])[C:14]=2[C:13]([CH3:27])=[C:12]1[C:28]1[CH:33]=[CH:32][C:31]([O:34][S:35]([CH2:38][CH2:39][C:40]([F:42])([F:43])[F:41])(=[O:36])=[O:37])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 166660063,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2-chloro-4-fluorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl ester

Product 1

HCID 578035873,3,3-Trifluoropropane-1-sulfonic acid 4-[1-(2-chloro-4-fluorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5-Dihydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl esterYield 29.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Bromine (39.0 mg, 0.244 mmol) dissolved in acetic acid (0.556 ml) was added to a solution of 4-[1-(2-chloro-4-fluorophenyl)-3-methyl-4-oxo-5-piperidin- 1-yl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenyl 3,3,3-trifluoropropane-1-sulfonate (75 mg, 0.122 mmol) (Example 3 ) in THF (3 ml) at −78° C. After 30 min at −78° C. the reaction mixture was allowed to reach rt. After 3 h at rt more bromine (19.5 mg, 0.122 mmol) dissolved in acetic acid (0.278 ml) was added and the reaction continued at rt for 5 h before the solvent was removed by evaporation. Purified by hplc to yield the title compound as a solid (22 mg, 29%).

Workup

  1. customto reach rt
  2. additionwas added
  3. waitthe reaction continued at rt for 5 h before the solvent
  4. customwas removed by evaporation
  5. customPurified by hplc

Sources & evidence

ORD record
ord-50f57ee3a657467e83a2f604abebd86d
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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