Cesium carbonate → 6-Amino-5-benzothiazol-2-yl-[3,4']bipyridinyl-2'-carboxylic acid methyl ester
Reaction equation
COC(=O)C1C=CC(C2C=NC(N)=C(C3SC4C=CC=CC=4N=3)C=2)=CC=1.[S:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]1[C:37]([NH2:51])=[N:38][CH:39]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:41]=1.[CH3:52][O:53][C:54]([C:56]1[CH:61]=[C:60](I)[CH:59]=[CH:58][N:57]=1)=[O:55].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[CH3:52][O:53][C:54]([C:56]1[CH:61]=[C:60]([C:40]2[CH:39]=[N:38][C:37]([NH2:51])=[C:36]([C:28]3[S:27][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[N:29]=3)[CH:41]=2)[CH:59]=[CH:58][N:57]=1)=[O:55]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Following the procedure for 4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-benzoic acid methyl ester, the title compound was prepared from 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (BB8) (1.41 g, 4.0 mmol), 4-iodopyridine-2-carboxylic acid methyl ester (0.85 g, 3.2 mmol), Pd(PPh3)4 (2 mol %) and Cs2CO3 (2.5 g, 7.7 mmol) in dioxane/water (5:1; 18 mL). 1H NMR (CD3OD, 300 MHz): δ=4.01 (s, 3H), 7.38-7.45 (m, 2H), 7.70 (dd, J=7.2, 2.4 Hz, 1H), 7.85 (d, J=6.8 Hz, 1H), 7.95 (d, J=6.8 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.31 (d, J=2.4 Hz, 1H), 8.44 (d, J=2.4 Hz, 1H), 8.70 (d, J=7.2 Hz, 1H).
Sources & evidence
- ORD record
- ord-49e39a8154a94179b139f7601454b6bf
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178668B2
Reaction notes
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