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

HRID 1698106노트

반응식

HRID 1698106 반응식
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]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 575534032-Chloro-1,3-benzothiazole-6-carboxamideHCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate

생성물 1

HCID 86626543Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate수율 47.7%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-94b465f84f4d4f65a2afb4115f57a524
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163928B2

반응 노트

불러오는 중…