Triphenylphosphine → HCID 86639063, compound

HRID 1019560Notes

Reaction equation

HRID 1019560 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:34]1[C:38]2=[N:39][CH:40]=[CH:41][CH:42]=[C:37]2[CH:36]=[CH:35]1.[CH3:43][CH2:44][C:45]([O-:47])=[O:46].[CH3:48][O:49][C:50]1[CH:51]=[C:52]([CH:55]=[CH:56][CH:57]=1)[CH2:53]O>O1CCCC1>[CH3:48][O:49][C:50]1[CH:51]=[C:52]([CH:55]=[CH:56][CH:57]=1)[CH2:53][N:34]1[C:38]2=[N:39][CH:40]=[CH:41][CH:42]=[C:37]2[CH:36]=[CH:35]1.[CH3:43][CH2:44][C:45]([O-:47])=[O:46]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 814373-Methoxybenzyl alcoholHCID 86639064HCID 86639064, compound

Product 1

HCID 86639063HCID 86639063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

0.089 mL (0.45 mmol) of diisopropyl azodicarboxylate is added dropwise under argon at 20° C., to a mixture of 260 mg (0.6 mmol) of supported triphenylphosphine (Argonaut PS—PPh3, loading 2.3 mmol/g), 57 mg (0.3 mmol) of 1H-pyrrolo[2,3-b]pyridine-2-ethyl carboxylate (WO07/010,138) and 62 mg (0.45 mmol) of 3-methoxybenzyl alcohol in 2.5 mL of tetrahydrofuran. The reactor is then sealed and the mixture is stirred for 3 days at 20° C. After this time, the reaction mixture is filtered, the solid residue is washed with 5 mL of tetrahydrofuran and the filtrate is concentrated at reduced pressure to give the expected product, which is used as it is in the rest of the synthesis.

Workup

  1. customThe reactor is then sealed
  2. filtrationAfter this time, the reaction mixture is filtered
  3. washthe solid residue is washed with 5 mL of tetrahydrofuran
  4. concentrationthe filtrate is concentrated at reduced pressure

Sources & evidence

ORD record
ord-6cea5226627a485ca35c65ab68168351
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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