Triphenylphosphine → HCID 90332545, compound

HRID 595766Notes

Reaction equation

HRID 595766 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[N:16]=[C:15]([C:17]3[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]4[O:24][C:23]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=4[CH:36]=3)[CH:14]=[CH:13][C:12]=1[CH2:43]O)[NH:6]2.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>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:11]4[N:16]=[C:15]([C:17]5[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:39])=[O:40])=[CH:19][C:20]6[O:24][C:23]([C:25]7[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=7)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=6[CH:36]=5)[CH:14]=[CH:13][C:12]=4[CH2:43][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 90332485HCID 90332485, compound

Product 1

HCID 90332545HCID 90332545, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(6-(4-fluoro-1H-indol-2-yl)-5-(hydroxymethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (280 mg, 0.45 mmol) was dissolved in THF (8 mL). To the resulting mixture was added diisopropyl azodicarboxylate (184 mg, 0.91 mmol) and PPh3 (238 mg, 0.91 mmol). The resulting mixture was stirred at RT overnight. Preparative TLC gave 5-(10-fluoro-5H-pyrido[2′,3′:3,4]pyrrolo[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (230 mg, yield: 85%) MS (M+H)+: 599.

Sources & evidence

ORD record
ord-51c89eaaa8654a21bc9557e514ef3acb
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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