Cesium carbonate → HCID 90389417、化合物

HRID 1526595ノート

反応式

HRID 1526595 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]#[N:22].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:21]([CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)#[N:22]

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 90389409HCID 90389409、化合物2 回

生成物 1

HCID 90389417HCID 90389417、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of methyl 5-hydroxy-3-methylpicolinate (0.8063 g, 4.82 mmol, step 3 intermediate 38) and cesium carbonate (0.772 ml, 9.65 mmol, Alfa Aesar) in DMF (48.2 ml) was added bromoacetonitrile (0.336 ml, 4.82 mmol, Sigma-Aldrich Chemical Company, Inc.). The reaction mixture was stirred for 4 h at rt. The reaction mixture was diluted with aqueous, saturated sodium bicarbonate solution and extracted with EtOAc. The organic extract was washed with aqueous, saturated sodium bicarbonate solution, brine and dried over MgSO4. The filtrate was concentrated in vacuo. MS m/z=207.1 [M+H]+. Calculated for C10H10N2O3: 206.069. 1H NMR (400 MHz, CHLOROFORM-d) ppm 2.67 (s, 3H) 3.98 (s, 3H) 4.88 (s, 2H) 7.20 (d, J=2.35 Hz, 1H) 8.32 (br. s., 1H)

後処理

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with aqueous, saturated sodium bicarbonate solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-6056093aba67434e8a4b8d05df977b76
出典データセット
uspto-grants-2015_07
特許番号
US09085576B2

反応ノート

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