(6-Fluoropyridin-3-yl)boronic acid → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1851757Notes

Reaction equation

HRID 1851757 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[S:8][C:4]=2[CH:3]=1.BrC1SC2C=C(OC)C=CC=2[N:24]=1.FC1C=CC(B(O)O)=CN=1>>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([NH2:24])[CH:18]=[CH:17][C:5]=3[N:6]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 112187652-Bromo-6-methoxy-1,3-benzothiazoleHCID 248037216-Bromo-2-(6-methoxypyridin-3-yl)-1,3-benzothiazole

Product 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

Procedure

The title compound was prepared according the method described for the preparation of 6-bromo-2-(6-methoxypyridin-3-yl)-1,3-benzothiazole, by reacting 2-bromo-6-methoxy-benzothiazole (1.09 g, 4.46 mmol) with 2-fluoropyridine-5-boronic acid (0.692 g, 4.9 mmol). The crude product was purified by flash column chromatography (0 to 2% methanol in DCM), to give the title compound (0.57 g). 1H NMR δ 8.88 (d, 1 H) 8.58 (td, 1H) 7.98 (d, 1 H) 7.76 (d, 1 H) 7.38 (dd, 1 H) 7.16 (dd, 1 H) 3.86 (s, 3 H); MS m/z (M+H) 261.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash column chromatography (0 to 2% methanol in DCM)

Sources & evidence

ORD record
ord-27d8519cd8ec4827a73971260f90d2ce
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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