4-(Trifluoromethyl)benzenesulfonyl chloride → 7-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2061613Notes

Reaction equation

HRID 2061613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][CH:14]3[NH:16][CH:10]([CH2:11][C:12](=[O:17])[CH2:13]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[F:18][C:19]([F:31])([F:30])[C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][CH:14]3[N:16]([S:26]([C:23]4[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:30])[F:31])=[CH:25][CH:24]=4)(=[O:28])=[O:27])[CH:10]([CH2:11][C:12](=[O:17])[CH2:13]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 673036667-(3-Bromophenyl)-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 673032167-(3-Bromophenyl)-9-(4-(trifluoromethyl)phenylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-oneYield 19%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

7-(3-Bromophenyl)-9-azabicyclo[3.3.1]nonan-3-one (90) and 4-(trifluoromethyl)benzene-1-sulfonyl chloride (12.25 g, 50.1 mmol) in pyridine (100 ml) and CH2Cl2 (100 ml) was stirred for 24 h. The solution was concentrated and flash chromatographed with CH2Cl2 as the eluant to yield 2.29 g (19% yield over 4 steps) of compound 91 as a pink solid.

Workup

  1. concentrationThe solution was concentrated
  2. customflash chromatographed with CH2Cl2 as the eluant

Sources & evidence

ORD record
ord-337143da13124f6d85d6c57f80682400
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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