Triphenylphosphine → HCID 178522481, compound

HRID 2280421Notes

Reaction equation

HRID 2280421 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6](/[N:8]=[C:9](\[NH:17][C:18]2[NH:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:19]=2)/[N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15]O)=[O:7])=[CH:4][CH:3]=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>C1COCC1>[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6](/[N:8]=[C:9]2\[NH:17][C:18]3[N:22]([N:21]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH:19]=3)[CH2:15][C@@H:11]3[CH2:12][CH2:13][CH2:14][N:10]\23)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178523890HCID 178523890, compound

Product 1

HCID 178522481HCID 178522481, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S,E)-4-fluoro-N-(((3-(4-fluorophenyl)-1H-pyrazol-5-yl)amino)(2-(hydroxymethyl)pyrrolidin-1-yl)methylene)benzamide (30 mg, 0.07 mmol) in anhydrous THF (0.4 mL) under a nitrogen atmosphere was added triphenylphosphine (22 mg, 0.085 mmol) followed by DIAD (16 μL, 0.085 mmol). The reaction mixture was stirred at room temperature for 30 minutes and purification by silica chromatography (EtOAc:hexanes) provided the title compound (22 mg, 77% yield). LCMS (ESI). found (M-H), 406.06. HPLC (Method A): 7.11 min.

Workup

  1. custompurification by silica chromatography (EtOAc:hexanes)

Sources & evidence

ORD record
ord-95ce9452d1e84127ad3e4cd877b113b8
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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