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

HRID 1698106ノート

反応式

HRID 1698106 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-94b465f84f4d4f65a2afb4115f57a524
出典データセット
uspto-grants-2012_04
特許番号
US08163928B2

反応ノート

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