Cesium carbonate → 3-Benzothiazol-2-ylpyridin-2-ylamine

HRID 1926336Notes

Reaction equation

HRID 1926336 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9](F)=[C:8]2C=1C=[C:5]([C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[N:6]=[CH:7]2.CC1(C)C(C)(C)OB(C2C(N)=NC=CC=2)O1.ClC1[S:38]C2C=CC=CC=2N=1.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>[S:38]1[C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=[C:5]1[C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 438110672-Aminopyridine-3-boronic acid, pinacol esterHCID 675212133-(5-Chloro-8-fluoroisoquinolin-3-yl)-pyridin-2-ylamine

Product 1

HCID 675209593-Benzothiazol-2-ylpyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared following the procedure for 3-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-2-ylamine, using 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (30.0 g, 136 mmol), 2-chlorobenzothiazole (16.5 g, 97 mmol), Pd(PPh3)4 (3.3 g, 3 mol %), and Cs2CO3 (72.6 g, 223 mmol). 1H NMR (CDCl3, 300 MHz): δ=6.71 (dd, J=6.8, 3.6 Hz, 1H), 7.13 (brs, 2H), 7.38 (t, J=8.4 Hz, 1H), 7.47 (t, J=8.4 Hz, 1H), 7.87 (d, J=6.0 Hz, 1H), 7.95 (dd, J=6.2, 1.5 Hz, 1H), 7.99 (d, J=6.0 Hz, 1H), 8.18 (dd, J=6.2, 1.2 Hz, 1H).

Sources & evidence

ORD record
ord-00649cf0b8e9426ab11dda8ec63e76c7
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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