Sodium Carbonate → 7-(2-Chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine

HRID 273509Notes

Reaction equation

Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (3.35 mmol, 1.0 equiv), 2-chloro-5-nitrophenyl-boronic acid (5.02 mmol, 1.5 equiv), Pd(PPh3)4 (0.335 mmol, 0.1 equiv), and Na2CO3 (13.4 mmol, 4.0 equiv) were dissolved in a mixture of DME/EtOH/H2O (4:1:1 v/v/v) and refluxed at 100° C. for 18 h. The reaction was diluted with 50 mL DCM and filtered. The precipitate was suspended in water to remove excess Na2CO3 and filtered again with a final Et2O wash to remove water. The crude precipitate gave 7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine, as a dark green solid (1.0 g, 94% yield). Rf=0.55 MS (ES+) m/z=316 LC retention time 2.96 min.

Workup

filtrationfiltered
customto remove excess Na2CO3
filtrationfiltered again with a final Et2O
washwash
customto remove water

Sources & evidence

ORD record: ord-aa05e8e29b7c4a2ebadae57442cbe427
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456176B2

Reaction notes

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