Cesium carbonate → N-[3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-benzyl]-methanesulfonamide

HRID 2409567ノート

反応式

HRID 2409567 の反応式
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[CH3:11][S:12]([NH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH2:16][NH:15][S:12]([CH3:11])(=[O:14])=[O:13])=[N:3]2)=[N:7][CH:8]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 22309453(3-{[(Methanesulfonyl)amino]methyl}phenyl)boronic acidHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 66717200N-[3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-benzyl]-methanesulfonamide収率 23.4%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
115 °C

実験手順

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.25 g, 0.757 mmol, 1 eq), (3-methanesulfonylaminomethylphenyl)boronic acid (0.208 g, 0.908 mmol, 1.2 eq), cesium carbonate (0.493 g, 1.514 mmol, 2 eq), Pd(PPh3)2Cl2 (0.053 g, 0.075 mmol, 0.1 eq), 1,4-dioxane (6 mL) and water (6 mL) was heated in a pressure tube at 115° C. for 4 h. Solvents were removed and the slurry obtained was partitioned between water and 10% MeOH in DCM. The organic layer was dried, filtered and evaporated. The residue was purified in an Isolute Flash Si II column (EtOAc) to give the desired product (77 mg, 23%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.04 min, [M+H]+ m/z 435.0.

後処理

  1. customSolvents were removed
  2. customthe slurry obtained
  3. customwas partitioned between water and 10% MeOH in DCM
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified in an Isolute Flash Si II column (EtOAc)

出典と根拠

ORDレコード
ord-fef5e99258494a0eb5c6768bb0db94ca
出典データセット
uspto-grants-2014_08
特許番号
US08815918B2

反応ノート

読み込み中…