Triphenylphosphine → HCID 86720577, compound

HRID 513206Notes

Reaction equation

HRID 513206 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][OH:13])=[CH:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]=12.[F:21][C:22]([F:32])([F:31])[O:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:27]3[CH:26]=[CH:25][C:24]([O:23][C:22]([F:21])([F:31])[F:32])=[CH:29][CH:28]=3)=[CH:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:7]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70015p-(Trifluoromethoxy)phenolHCID 5363146Diisopropyl azodicarboxylateHCID 86720578HCID 86720578, compound

Product 1

HCID 86720577HCID 86720577, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 7-chloro-3-(2-hydroxyethyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (233 mg, 0.79 mmol) in PhMe (15 mL) was added 4-trifluoromethoxyphenol (0.15 mL, 1.2 mmol), triphenylphosphine (309 mg, 1.2 mmol), and diisopropylazodicarboxylate (0.23 mL, 1.2 mmol) at r.t. After 20 min, the mixture was concentrated in vacuo, and the crude material was purified on silica (gradient elution, 0-30% EtOAc/hexanes) to yield the title product (349 mg). HRMS (ESI) calc (M+H)+=457.1136. found 457.1133.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe crude material was purified on silica (gradient elution, 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6944b3299ea24086a180d73923f76289
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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