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

HRID 1427161Notes

Reaction equation

HRID 1427161 reaction equation
[N:1]1[C:6]2[CH:7]3[CH2:12][NH:11][CH2:10][CH2:9][N:8]3[C:13](=[O:14])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Br:24][C:25]1[CH:30]=[C:29]([C:31]([F:33])([F:32])[F:34])[CH:28]=[CH:27][C:26]=1[S:35]([N:11]1[CH2:10][CH2:9][N:8]2[C:13](=[O:14])[C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:6]=3[CH:7]2[CH2:12]1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27786112-Bromo-4-(trifluoromethyl)benzenesulfonyl chlorideHCID 70557780HCID 70557780, compound2×

Product 1

HCID 705582489-{[2-Bromo-4-(trifluoromethyl)phenyl]sulfonyl}-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8,9,10,10a-tetrahydropyrido[2′,3′:3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one (may be prepared as in Intermediate 7, 130 mg) in DCM (5 mL) was added DIPEA (0.360 mL, 2.061 mmol). The mixture was cooled to 0° C. and 2-bromo-4-(trifluoromethyl)benzenesulfonyl chloride (233 mg) was added.

Sources & evidence

ORD record
ord-0e86cf92b78a4d94b7e8bcdde6112359
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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