Dichloromethane → 2-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-8-(2-acetylethyl)-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepine

HRID 232884

Reaction equation

HRID 232884 reaction equation
[CH3:1][CH:2]([OH:5])[CH:3]=[CH2:4].C(N(CC)CC)C.[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:48]=[CH:47][C:29]4[O:30][CH2:31][C:32]5[CH:45]=[C:44](I)[CH:43]=[CH:42][C:33]=5[CH:34]([O:35][CH:36]5[CH2:41][CH2:40][CH2:39][CH2:38][O:37]5)[C:28]=4[CH:27]=3)=[N:21]2)=[CH:16][C:15]=1[F:49].C(Cl)Cl>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20]([CH2:24][O:25][C:26]3[CH:48]=[CH:47][C:29]4[O:30][CH2:31][C:32]5[CH:45]=[C:44]([CH2:4][CH2:3][C:2](=[O:5])[CH3:1])[CH:43]=[CH:42][C:33]=5[CH:34]([O:35][CH:36]5[CH2:41][CH2:40][CH2:39][CH2:38][O:37]5)[C:28]=4[CH:27]=3)=[N:21]2)=[CH:16][C:15]=1[F:49]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 117163-Buten-2-olHCID 233591512-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-8-iodo-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 233591482-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-8-(2-acetylethyl)-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepineYield 61.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

0.2 g of (±)-3-buten-2-ol, 1.4 mg of palladium (II) acetate and 0.27 g of triethylamine were added to 1.36 g of 2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-8-iodo-11-(2-tetrahydropyranyloxy)-6,11-dihydrodibenz[b,e]oxepine obtain in Reference example 73 dissolved in 2.5 ml of acetonitrile and the mixture was refluxed under heating for 5.5 hours. After 60 ml of methylene chloride and 60 ml of ice water were added to this reaction mixture, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. After the solvent was removed, the residue was applied to silica gel column chromatography to obtain 0.76 g of the title compound.

Workup

  1. customobtain in Reference example 73
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 5.5 hours
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter the solvent was removed

Sources & evidence

ORD record
ord-dea302f230154be58f444459c1e69e67
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Linked notes

Loading…