3-(Trifluoromethyl)phenol → HCID 86589038, compound

HRID 1743928Notes

Reaction equation

HRID 1743928 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N:15]1([C:22]2[C:31]3[C:26](=[CH:27][C:28]([CH2:33][OH:34])=[C:29]([CH3:32])[CH:30]=3)[N:25]=[C:24]([Cl:35])[CH:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[F:36][C:37]([F:46])([F:45])[C:38]1[CH:39]=[C:40](O)[CH:41]=[CH:42][CH:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.C(OCC)(=O)C>[N:15]1([C:22]2[C:31]3[C:26](=[CH:27][C:28]([CH2:33][O:34][C:42]4[CH:41]=[CH:40][CH:39]=[C:38]([C:37]([F:46])([F:45])[F:36])[CH:43]=4)=[C:29]([CH3:32])[CH:30]=3)[N:25]=[C:24]([Cl:35])[CH:23]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86589037HCID 86589037, compound

Product 1

HCID 86589038HCID 86589038, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylazodicarboxylate (66 mg, 0.33 mmol) was added dropwise at r.t. to a solution of (4-Azepan-1-yl-2-chloro-6-methyl-quinolin-7-yl)-methanol (example 82, 100 mg, 0.33 mmol), 3-trifluoromethylphenol (53 mg, 0.33 mmol), and triphenylphosphine (86 mg, 0.33 mmol) in dichloromethane (2 mL), then after 2 h ethyl acetate was added and the solution was washed with 1 M aq. sodium hydroxide solution and brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate gradient) yielded the title compound (118 mg, 80%). White solid, ISP-MS: m/e=449.4 ([M+H]+).

Workup

  1. washthe solution was washed with 1 M aq. sodium hydroxide solution and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-a99e347e6c9149aeb7fd606c1a8805cf
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

Loading…