2-Bromo-4-(trifluoromethyl)benzenesulfonyl chloride → 9-{[2-Bromo-4-(trifluoromethyl)phenyl]sulfonyl}-2-methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one

HRID 1427162Notes

Reaction equation

HRID 1427162 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13](=[O:14])[N:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH:7]3[C:6]=2[N:15]=1.[Br:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>ClCCl.CCN(C(C)C)C(C)C>[Br:16][C:17]1[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[CH:19][C:18]=1[S:27]([N:11]1[CH2:10][CH2:9][N:8]2[C:13](=[O:14])[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[N:15][C:6]=3[CH:7]2[CH2:12]1)(=[O:29])=[O:28]

Participants

5

Reactant 2

HCID 27786112-Bromo-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 705575122-Methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one2×

Product 1

HCID 681754379-{[2-Bromo-4-(trifluoromethyl)phenyl]sulfonyl}-2-methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-oneYield 70.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To the solution of 2-methyl-8,9,10,10a-tetrahydropyrido[2′,3′:3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one (may be prepared as described in Intermediate 8; 100 mg) in dichloromethane (3.5 ml), DIPEA (0.129 ml) was added under argon atmosphere at room temperature then 2-bromo-4-(trifluoromethyl)benzenesulfonyl chloride (159 mg) was added at 0° C., and then the ice water bath was removed and the reaction mixture allowed to stir at room temperature for 3 h. The reaction mixture was partitioned between DCM (40 ml) and (20 ml) sodium bicarbonate. The organic phase was washed with sodium bicarbonate (20 ml), HCl (2×20 ml) and water (2×20 ml) and then it was dried using phase separator before the DCM was removed under vacuum to give the title compound (170 mg), which was used in next step without purification.

Workup

  1. customthe ice water bath was removed
  2. customThe reaction mixture was partitioned between DCM (40 ml) and (20 ml) sodium bicarbonate
  3. washThe organic phase was washed with sodium bicarbonate (20 ml), HCl (2×20 ml) and water (2×20 ml)
  4. customit was dried
  5. customwas removed under vacuum

Sources & evidence

ORD record
ord-e7c190d131904b21b9141f57de47801f
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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