Triphenylphosphine → 7-(1-Tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline

HRID 454088Notes

Reaction equation

HRID 454088 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([CH3:22])=[CH:16]4)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:43][CH:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[C:53]([O:52][C:50]([N:47]1[CH2:48][CH2:49][CH:44]([CH2:43][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:14]=[C:15]5[C:19](=[CH:20][CH:21]=4)[NH:18][C:17]([CH3:22])=[CH:16]5)=[N:7][CH:8]=[N:9]3)=[CH:4][CH:3]=2)[CH2:45][CH2:46]1)=[O:51])([CH3:56])([CH3:54])[CH3:55]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 1357631147-Hydroxy-4-(2-methylindol-5-yloxy)quinazoline

Product 1

HCID 220308467-(1-Tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazolineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-hydroxy-4-(2-methylindol-5-yloxy)quinazoline (423 mg, 1.45 mol), (prepared as described for the starting material in Example 82), triphenylphosphine (685 mg, 2.61 mmol), 4-hydroxymethyl-1-tert-butoxycarbonylpiperidine (500 mg, 2.32 mmol), (prepared as described for the starting material in Example 10), and diisopropyl azodicarboxylate (528 mg, 2.61 mmol) in methylene chloride (18 ml) was stirred overnight at ambient temperature. The mixture was then poured onto a column of silica and eluted with ethyl acetate. After evaporation of the solvent, the residue was triturated with ether, filtered, and dried under vacuum to give 7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline (478 mg, 68%).

Workup

  1. custom(prepared
  2. additionThe mixture was then poured onto a column of silica
  3. washeluted with ethyl acetate
  4. customAfter evaporation of the solvent
  5. customthe residue was triturated with ether
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-9bf2a2f950c3416e9c5c109d5904664f
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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