3,4-Dichlorophenol → HCID 24771573, compound

HRID 1429599Notes

Reaction equation

HRID 1429599 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[Cl:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:27][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 57425298HCID 57425298, compound

Product 1

HCID 24771573HCID 24771573, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (6-bromo-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone (76.7 mg, 0.25 mmol) in DMF (2.5 mL) was added 3,4 dichlorophenol (40.07 mg, 0.25 mmol) and K2CO3 (101.93 mg, 0.74 mmol). After 18 h at 120° C., the mixture was cooled to rt, diluted with water, and extracted with DCM. Purification by FCC followed by reverse phase HPLC (basic conditions) provided the desired product (10.0 mg, 3.5%). MS (ESI): mass calcd. for C19H21Cl2N3O2, 393.10; m/z found, 394.3 [M+H]+. 1H NMR (CDCl3): 7.82 (dd, J=8.2, 7.4 Hz, 1H), 7.52-7.44 (m, 2H), 7.26 (d, J=2.7 Hz, 1H), 7.06-6.98 (m, 2H), 3.75-3.67 (m, 2H), 3.50-3.44 (m, 2H), 2.70-2.61 (m, 1H), 2.55-2.48 (m, 2H), 2.23-2.15 (m, 2H), 1.01 (d, J=6.6 Hz, 6H).

Workup

  1. extractionextracted with DCM
  2. customPurification by FCC

Sources & evidence

ORD record
ord-5bc94c4c5a5e42e7b37c6bebdae4d0fd
Source dataset
uspto-grants-2015_01
Patent number
US08940731B2

Reaction notes

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