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

HRID 501049

反応式

HRID 501049 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a032e3afb19e418595dd11b2e977e424
出典データセット
uspto-grants-2010_08
特許番号
US07772256B2

関連ノート

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