Benzo(B)Thiophene-2-Boronic Acid → 5-(1-Benzothien-2-yl)pyridine-2-carboxamide

HRID 501049

반응식

HRID 501049 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.Br[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1.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]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1

참가 물질

6

반응물 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 7351515-Bromopyridine-2-carboxamide

생성물 1

HCID 250149305-(1-Benzothien-2-yl)pyridine-2-carboxamide수율 3.6%

시약·촉매·용매 2

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

실험 절차

2-Benzothienylboronic acid (1.8 mmol), 5-bromopyridine-2-carboxamide (1.2 mmol), 2M K2CO3 (2.4 mL), Pd(dppf)Cl2 (0.12 mmol) were mixed and stirred at 80° C. in DMF for 3 h. The reaction mixture was filtered and to the filtrated was added EtOAc and H2O. The layers were separated and the aqueous phase was extracted twice with EtOAc. The organic extracts were dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid. The crude was subjected to reverse phase HPLC to afford the title compound as a light brown solid (11 mg). 1H NMR δ ppm 9.07 (d, 1 H) 8.34 (dd, 1 H) 8.24-8.02 (m, 5 H) 7.73 (s br, 1 H) 7.54-7.37 (m, 2 H); MS m/z 255 (M+H).

후처리

  1. filtrationThe reaction mixture was filtered and to the filtrated
  2. additionwas added EtOAc and H2O
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. customThe solvent was evaporated in vacuo
  7. customto give a brown solid

출처 및 근거

ORD 기록
ord-a032e3afb19e418595dd11b2e977e424
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772256B2

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