Triphenylphosphine → 4-Chloro-6-cyano-7-(2-(tetrahydropyran-4-yloxy)ethoxy)quinoline

HRID 2222416Notes

Reaction equation

HRID 2222416 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.O[CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][O:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 597122412-(Oxan-4-yloxy)ethan-1-ol2×HCID 1355837304-Chloro-6-cyano-7-hydroxyquinoline

Product 1

HCID 691365844-Chloro-6-cyano-7-(2-(tetrahydropyran-4-yloxy)ethoxy)quinolineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-6-cyano-7-hydroxyquinoline (400 mg, 1.95 mmol), (prepared as described for the starting material in Example 1), 4-(2-hydroxyethoxy)tetrahydropyran (371 mg, 2.54 mmol) and triphenylphosphine (820 mg, 3.12 mmol) in methylene choride (15 ml) was added diethyl azodicarboxylate (492 μl, 3.12 mmol) in portions. After stirring for 30 minutes, triphenylphosphine (512 mg, 1.95 mmol), 4-(2-hydroxyethoxy)-tetrahydropyran (142 mg, 0.98 mmol) and diethyl azodicarboxylate (308 μl, 1.95 mmol) were added. The volatiles were removed under vacuum and the residue was purified by column chrolatography eluting with methylene chloride/ethyl actetate/methanol (60/40/0 followed by 50/50/0, 40/60/0, 60/39/1, 60/38/2 and 50/46/4) to give 4-chloro-6-cyano-7-(2-(tetrahydropyran-4-yloxy)ethoxy)quinoline (519 mg, 65%).

Workup

  1. custom(prepared
  2. customThe volatiles were removed under vacuum
  3. customthe residue was purified by column chrolatography
  4. washeluting with methylene chloride/ethyl

Sources & evidence

ORD record
ord-13096f4dc8654f7db23340b734b08112
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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