2-Chlorobenzothiazole → tert-Butyl [5-(1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

HRID 1698099Notes

Reaction equation

HRID 1698099 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16](=[O:33])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22](B2OCC(C)(C)CO2)=[CH:21][N:20]=1)([CH3:14])([CH3:13])[CH3:12].COC1C=CC2N=C(C3C=NC(N)=NC=3)SC=2C=1>>[C:11]([O:15][C:16](=[O:33])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:21][N:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 248040695-(6-Methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amineHCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate

Product 1

HCID 86626542tert-Butyl [5-(1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamateYield 62.1%

Procedure

2-Chlorobenzothiazole (31 μL, 0.25 mmol) and tert-butyl[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (80 mg, 0.25 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine. After 1 h at 80° C., the mixture was concentrated under reduced pressure and the residue was partitioned between DCM and H2O. The organic phase was concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (53 mg) as a white solid. MS m/z (M+H) 342.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between DCM and H2O
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-7f2e3f2f4682411ab1bddc315c82a34e
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

Loading…