Cesium carbonate → Methyl 3-[6-Amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-benzoate
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](C2C=CC(C(OC)=O)=CC=2)=[CH:4][C:3]=1[C:18]1[N:19]=[CH:20][C:21]2[C:26]([CH:27]=1)=[C:25]([Cl:28])[CH:24]=[CH:23][C:22]=2[F:29].BrC1C=C(C2N=CC3C(C=2)=C(Cl)C=CC=3F)C(N)=NC=1.[C:50]([C:54]1[CH:55]=[C:56](B(O)O)[CH:57]=[CH:58][CH:59]=1)([O:52][CH3:53])=[O:51].C([O-])([O-])=O.[Cs+].[Cs+]>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>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:58]2[CH:59]=[C:54]([CH:55]=[CH:56][CH:57]=2)[C:50]([O:52][CH3:53])=[O:51])=[CH:4][C:3]=1[C:18]1[N:19]=[CH:20][C:21]2[C:26]([CH:27]=1)=[C:25]([Cl:28])[CH:24]=[CH:23][C:22]=2[F:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the procedure for methyl 4-[6-amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-benzoate, the title compound was prepared from 5-bromo-3-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-2-ylamine (BB4) (0.4 g, 1.13 mmol), 3-(carbomethoxy)phenylboronic acid (0.214 g, 1.2 mmol), Pd(PPh3)4 (5 mol %) and Cs2CO3 (0.89 g, 2.3 mmol). 1H NMR (CDCl3, 300 MHz): δ=6.59 (bs, 2H), 7.20 (dd, J=8.4, 7.8 Hz, 1H), 7.55 (t, J=7.8 Hz, 1H), 7.43 (dd, J=5.2, 4.8 Hz, 1H), 7.80 (dd, J=6.8, 2.4 Hz, 1H), 8.01 (dd, J=6.8, 2.4 Hz, 1H), 8.17 (d, J=2.1 Hz, 1H), 8.28 (t, J=1.8 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 9.59 (s, 1H).
Sources & evidence
- ORD record
- ord-44cc517a48ef47c1af5d12956ede5f84
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178668B2
Reaction notes
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