4-Bromo-2-chloroaniline → HCID 68291258, compound

HRID 2205923Notes

Reaction equation

HRID 2205923 reaction equation
[CH3:1][N:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=[N:3]1.Br[C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([Cl:24])[CH:18]=1>COCCOC.CO>[Cl:24][C:19]1[CH:18]=[C:17]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH:23]=[CH:22][C:20]=1[NH2:21]

Participants

4

Reactant 2

HCID 6101694-Bromo-2-chloroanilineHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 68291258HCID 68291258, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 86595564Dimethoxyethane methanolSolvent

Procedure

Prepared using Method C (Preparation 85) using 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-2-chloroaniline in DME/MeOH 2/1 for 10 minutes at 150° C. under microwave irradiation. Purified using silica gel column chromatography eluting with 20% hexane in ethyl acetate to afford the title compound as a white powder (77 mg, 74%). 1H-NMR (500 MHz, CDCl3): δ 3.86 (s, 3H), 4.26 (s, br, 2H), 6.22 (d, J=2 Hz, 1H), 6.81 (d, J=8.3 Hz, 1H), 7.1 (dd, J=2 Hz, 8.3 Hz. Hz, 1H), 7.31 (d, J=2.0 Hz, 1H), 7.48 (d, J=2 Hz, 1H).

Workup

  1. customPrepared
  2. customMethod C (Preparation 85)
  3. customfor 10 minutes
  4. customat 150° C.
  5. customunder microwave irradiation
  6. customPurified
  7. washeluting with 20% hexane in ethyl acetate

Sources & evidence

ORD record
ord-8ad061ffe2ad42d8b23188e8ad5cedae
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

Loading…