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

HRID 595760
Notes
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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
ParticipantsProcedureSources & evidenceReaction notes

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 8028Tetrahydrofuran
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09243002B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes