2,6-Lutidine → HCID 86691230, compound

HRID 880224Notes

Reaction equation

HRID 880224 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH2:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1.N1C(C)=CC=CC=1C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH:18][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]([F:16])([F:17])[F:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 12164755(S)-1-(4-Bromophenyl)-2,2,2-trifluoroethanamine

Product 1

HCID 86691230HCID 86691230, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Add methanesulfonyl chloride (16.42 mL, 0.21 mol) drop-wise to a mixture of (1S)-1-(4-bromophenyl)-2,2,2-trifluoroethanamine (49 g, 0.19 mol), 4-dimethylaminopyridine (1.18 g, 9.0 mmol), 2,6-lutidine (67 mL, 0.57 mol) in DCM (250 mL) at 0° C. Warm the mixture to ambient temperature and stir at that temperature for 20 hours. Dilute the reaction mixture with DCM (300 mL) and wash it sequentially with 2M HCl (2×200 mL), water (250 mL), then brine (250 mL). Collect the organic phase and dry over magnesium sulphate; filter; and concentrate the filtrate under reduced pressure. Triturate the residue with hexane (200 mL) for 10 min; filter; and dry the solid under reduced pressure to give the title compound as a pale brown solid (60 g, 93% yield, 98% ee). MS (m/z): 332 (M+1).

Workup

  1. washwash it sequentially with 2M HCl (2×200 mL), water (250 mL)
  2. customCollect the organic phase
  3. dry with materialdry over magnesium sulphate
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customTriturate the residue with hexane (200 mL) for 10 min
  7. filtrationfilter
  8. customand dry the solid under reduced pressure

Sources & evidence

ORD record
ord-2b1212bbe5fe4e188bb7314671b67894
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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