Triphenylphosphine → HCID 86756032, compound

HRID 1857496Notes

Reaction equation

HRID 1857496 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH2:22]([O:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([CH2:37]O)[CH:35]=2)[C@H:30]([N:41]([CH2:46][C:47]2[CH:52]=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:50]=[C:49]([C:57]([F:60])([F:59])[F:58])[CH:48]=2)[C:42]([O:44][CH3:45])=[O:43])[CH2:29][C@@H:28]1[CH3:61])=[O:26])[CH3:23]>ClCCl.C(Cl)(Cl)Cl>[CH2:22]([O:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([CH2:37][Br:20])[CH:35]=2)[C@H:30]([N:41]([CH2:46][C:47]2[CH:52]=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:50]=[C:49]([C:57]([F:60])([F:59])[F:58])[CH:48]=2)[C:42]([O:44][CH3:45])=[O:43])[CH2:29][C@@H:28]1[CH3:61])=[O:26])[CH3:23]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 86756027HCID 86756027, compound

Product 1

HCID 86756032HCID 86756032, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (0.457 g, 1.74 mmol) in anhydrous dichloromethane (15 mL) at 0° C. was slowly added bromine (84 μL, 1.6 mmol). After the reaction was stirred at 0° C. for 20 min, a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-hydroxymethyl-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 85) (0.630 g, 1.09 mmol) in dichloromethane (15 ml) was added. The reaction was stirred at 0° C. for 20 min, then at room temperature for 3 h. The reaction mixture was then diluted with chloroform and washed with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 10-15% ethyl acetate/hexanes as eluent afforded the title product (0.500 g, 72%): MS m/z 642.1 (M+ +1); 1H NMR (CDCl3) δ 1.15 (d, 3H), 1.3 (t, 3H), 3.8 (s, 3H), 3.85 (s, 3H), 6.4 (s, 1H), 7.4 (s, 1H), 7.7 br, 2H), 7.8 (s, 1H).

Workup

  1. customat 0° C.
  2. stirringThe reaction was stirred at 0° C. for 20 min
  3. waitat room temperature for 3 h
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-bb5bf1f385f44266be5311500f988c0f
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

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