Tetrahydrofuran → 1-(4-Chloro-3',5'-difluoro-5-methyl-6-pyridin-4-ylbiphenyl-2-yl)ethanamine

HRID 510893Notes

Reaction equation

HRID 510893 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:5]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[C:4]([C:23](=O)[CH3:24])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:32].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:5]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[C:4]([CH:23]([NH2:32])[CH3:24])[CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 866668121-(4-Chloro-3',5'-difluoro-5-methyl-6-pyridin-4-ylbiphenyl-2-yl)ethanone

Product 1

HCID 866668131-(4-Chloro-3',5'-difluoro-5-methyl-6-pyridin-4-ylbiphenyl-2-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-chloro-3′,5′-difluoro-5-methyl-6-pyridin-4-ylbiphenyl-2-yl)ethanone (0.013 g, 0.036 mmol), ammonium acetate (0.028 g, 0.36 mmol) and 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.091 mL, 0.091 mmol) in methanol (0.1 mL) and acetonitrile (0.1 mL) was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to give the desired product. LCMS calculated for C20H18ClF2N2 (M+H)+: m/z=359.1. found: 359.1.

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6aa5ded9a35146a9bfb694ec4e39fab7
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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