Dicyclohexylcarbodiimide → 8,9-dimethoxy-6-[4'-(4,4,5,5,6,6,7,7,7-nonafluoroheptanoyloxy)biphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran

HRID 2090520Notes

Reaction equation

HRID 2090520 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:9]1[O:10][CH2:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH:13]=[C:8]1[CH:7]=[C:6]2[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48]O)=[CH:44][CH:43]=2)=[CH:38][CH:37]=1.[F:50][C:51]([F:67])([C:57]([F:66])([F:65])[C:58]([F:64])([F:63])[C:59]([F:62])([F:61])[F:60])[CH2:52][CH2:53][C:54](O)=[O:55].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:9]1[O:10][CH2:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH:13]=[C:8]1[CH:7]=[C:6]2[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48][C:54](=[O:55])[CH2:53][CH2:52][C:51]([F:50])([F:67])[C:57]([F:65])([F:66])[C:58]([F:63])([F:64])[C:59]([F:60])([F:62])[F:61])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 108035372H,2H,3H,3H-Perfluoroheptanoic acidHCID 1317305668,9-dimethoxy-6-[4'-hydroxyoxybiphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran

Product 1

HCID 1317305658,9-dimethoxy-6-[4'-(4,4,5,5,6,6,7,7,7-nonafluoroheptanoyloxy)biphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyranYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 8,9-dimethoxy-6-[4′-hydroxyoxybiphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran (0.95 g, 1.5 mmol) and 4,4,5,5,6,6,7,7,7-nonafluoroheptanoic acid (0.53 g, 1.8 mmol) in DCM (20 mL) containing 4-dimethylaminopyridine (0.02 g) and N,N′-dicyclohexylcarbodiimide (0.33 g, 1.6 mmol) under N2 was stirred at room temperature for 1 h. The resulting mixture was filtered through a short plug of silica using EtOAc (5% in DCM) as eluent. The solvent was removed under reduced pressure and the residue chromatographed on silica using EtOAc (0-25% gradient in toluene) as eluent. The solvent was removed under reduced pressure and the residue washed with toluene/hexanes to give the title compound (0.69 g, 51%) as a pale violet powder, mp 218-219° C. The liquors provided a further 0.16 g (12%) after evaporation and washing with acetone.

Workup

  1. filtrationThe resulting mixture was filtered through a short plug of silica
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed on silica
  4. customThe solvent was removed under reduced pressure
  5. washthe residue washed with toluene/hexanes

Sources & evidence

ORD record
ord-a2c0e34fbcde437cae80fd9f9230fb69
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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