4-Bromo-2-chloroaniline → HCID 68290593, compound

HRID 2205903Notes

Reaction equation

HRID 2205903 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([Cl:9])[CH:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](B(O)O)[CH:11]=1>>[Cl:9][C:4]1[CH:3]=[C:2]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:5]=1[NH2:6]

Participants

3

Reactant 2

HCID 6101694-Bromo-2-chloroanilineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 68290593HCID 68290593, compoundYield 94%

Procedure

Prepared according to Method C (Preparation 85) using 4-bromo-2-chloroaniline and pyridin-3-ylboronic acid. Purified using Biotage silica gel column chromatography eluting with DCM/EtOH 99/1 to 97/3 and filtered on SCX-2 column to afford the title product as a yellow oil (93 mg, 94%). 1H NMR (500 MHz, CDCl3): δ 3.96 (br s, 2H), 6.87 (d, J=8.2 Hz, 1H), 7.32 (dd, J=8.2, 2.2 Hz, 1H), 7.35 (ddd, J=7.9, 4.8, 1.0 Hz, 1H), 7.51 (d, J=2.2 Hz, 1H), 7.80 (ddd, J=7.9, 2.3, 1.6 Hz, 1H), 8.54 (dd, J=4.8, 1.6 Hz, 1H), 8.79 (dd, J=2.3, 1.0 Hz, 1H).

Workup

  1. customPrepared
  2. customaccording to Method C (Preparation 85)
  3. customPurified
  4. washeluting with DCM/EtOH 99/1 to 97/3
  5. filtrationfiltered on SCX-2 column

Sources & evidence

ORD record
ord-aa0a292c69084aeb960f3b80ab2c2012
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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