Water → 144991-53-7
Reaction equation
Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5](Br)[C:3]=1N.CB1OB(C)OB(C)O1.[C:23](=O)([O-])[O-].[K+].[K+].O.C[N:31]([CH:33]=O)C>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>[CH3:23][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[C:5]([CH3:3])[C:33]=1[NH2:31]Participants
7
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 2,6-dibromo-4-trifluoromethyl aniline (1.00 g, 3.14 mmol), trimethylboroxine (1.16 ml, 1.04 g, 8.33 mmol), potassium carbonate (1.15 g, 8.33 mmol) and catalytic amount (10%) Pd(PPh3)4 in DMF (5 ml) was heated to 90° C. for 14 h. Water (10 ml) was added. The mixture was extracted with ethyl acetate (3×20 ml). The combined EtOAc layers were washed with brine and dried over sodium sulfate. The titled compound was obtained as a colorless oil after a flash column using EtOAc:hexane (1:9) as the elute. 1H NMR (CDCl3, 500 M): δ 7.28 (s, 1H), 7.22 (s, 1H), 3.88 (br s, 2H), 2.21 (s, 6H).
Workup
- extractionThe mixture was extracted with ethyl acetate (3×20 ml)
- washThe combined EtOAc layers were washed with brine
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-c07b929e510344b6ab58a84d19902801
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652049B2
Reaction notes
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