Cesium carbonate → 2-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione

HRID 244815

反応式

HRID 244815 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[CH2:26]([N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40])[CH2:27][CH:28]=[CH2:29].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:5]3[CH:4]=[CH:3][C:2](/[CH:29]=[CH:28]/[CH2:27][CH2:26][N:30]4[C:38](=[O:39])[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:31]4=[O:40])=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:12]=1)[CH3:25]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 339432N-(3-Buten-1-yl)phthalimideHCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 690842002-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione収率 77.1%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (1.9 g, 4.68 mmol), 2-but-3-enyl-1H-isoindole-1,3(2H)-dione (1.04 g, 5.15 mmol), cesium carbonate (3.05 g, 9.36 mmol), triphenylphosphine (0.246 g, 0.94 mmol), palladium(II) acetate (0.105 g, 0.47 mmol), and N,N-dimethylformamide (DMF) (28 mL) were added to a pressure tube. The vessel was sealed with a TEFLON cap and heated at 140° C. for 2.5 hours. The reaction was cooled to ambient temperature. The reaction was diluted with ethyl acetate and washed multiple times with water. The initial water wash was extracted with ethyl acetate. The organic fractions were combined and washed with water once again. The organic fractions were concentrated under reduced pressure and the residue was purified using a HORIZON HPFC system (silica cartridge, eluting with a linear gradient of 2-20% CMA in chloroform) to yield 1.9 g of 2-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione as a pale yellow oil.

後処理

  1. customcap
  2. temperatureThe reaction was cooled to ambient temperature
  3. washwashed multiple times with water
  4. washThe initial water wash
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water once again
  7. concentrationThe organic fractions were concentrated under reduced pressure
  8. customthe residue was purified
  9. washeluting with a linear gradient of 2-20% CMA in chloroform)

出典と根拠

ORDレコード
ord-ee3b73b30ec64502ba910176f53a7759
出典データセット
uspto-grants-2014_02
特許番号
US08658666B2

関連ノート

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