Triphenylphosphine → 7-(1-Tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxycinnoline

HRID 2180130Notes

Reaction equation

HRID 2180130 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[Cl:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[N:16][CH:15]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([CH2:40]O)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([CH2:40][O:26][C:20]2[CH:19]=[C:18]3[C:23]([C:14]([Cl:13])=[CH:15][N:16]=[N:17]3)=[CH:22][C:21]=2[O:24][CH3:25])[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 1357525234-Chloro-7-hydroxy-6-methoxycinnoline

Product 1

HCID 224900187-(1-Tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxycinnolineYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DEAD (1.46 g, 8.38 mmol) was added to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (1.47 g, 6.98 mmol), (prepared as described for the starting material in Example 1), 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (1.65 g, 7.68 mmol), (prepared as described for the starting material in Example 6), and triphenylphosphine (2.74 g) in methylene chloride (40 ml). The mixture was stirred for 1 hour at ambient temperature, then poured onto silica and eluted with a gradient of ethyl acetate in methylene chloride (30/70 to 50/50). The fractions containing the expected product were combined and evaporated to give 7-(1-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxycinnoline (561 mg, 58%).

Workup

  1. custom(prepared
  2. custom(prepared
  3. additionpoured onto silica
  4. washeluted with a gradient of ethyl acetate in methylene chloride (30/70 to 50/50)
  5. additionThe fractions containing the expected product
  6. customevaporated

Sources & evidence

ORD record
ord-dfb0fc72a6334d7f934defbd52b0d57a
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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