Triphenylphosphine → 2-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine

HRID 595760Notes

Reaction equation

HRID 595760 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[C:5]([CH2:18][CH2:19]O)=[CH:4][CH:3]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[C:14]([F:17])[C:15]=4[CH:16]=[C:8]3[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 903336162-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethanol

Product 1

HCID 903336312-Chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethanol (60 mg, 0.21 mmol) was dissolved in THF (4 ml). To the resulting mixture was added diisopropyl azodicarboxylate (42 mg, 0.21 mmol) and PPh3 (54 mg, 0.21 mmol). The resulting mixture was stirred at RT overnight. Preparative TLC gave 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (50 mg, yield: 89%) MS (M+H)+: 273.

Sources & evidence

ORD record
ord-fb19bbe499254498909426d4d2313ea7
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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