Potassium Carbonate → Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

HRID 1698106Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:14]([O:18][C:19](=[O:36])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OCC(C)(C)CO2)=[CH:24][N:23]=1)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:14]([O:18][C:19](=[O:36])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([C:11](=[O:12])[NH2:13])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:24][N:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-1,3-benzothiazole-6-carboxamide (77 mg, 0.36 mmol), tert-butyl[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (0.174 g, 0.54 mmol), Pd(dppf)Cl2*DCM (30 mg, 0.036 mmol) and 2 M aq. K2CO3 (0.8 mL) in DMF (2 mL) was stirred under argon at 80° C. for 2 h. The reaction mixture was filtered and the filtrate was partitioned between EtOAc and H2O. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (66 mg) as a white solid. MS m/z (M−H) 383.

Workup

filtrationThe reaction mixture was filtered
customthe filtrate was partitioned between EtOAc and H2O
customThe layers were separated
extractionthe aqueous phase was extracted with EtOAc
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-94b465f84f4d4f65a2afb4115f57a524
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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