Cesium carbonate → HCID 90389417, 화합물

HRID 1526595노트

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HRID 1526595 반응식
[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]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 90389409HCID 90389409, 화합물2회

생성물 1

HCID 90389417HCID 90389417, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-6056093aba67434e8a4b8d05df977b76
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

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