Triphenylphosphine → HCID 90341041, compound

HRID 595771Notes

Reaction equation

HRID 595771 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[CH:43]([F:46])[CH2:44]O)[NH:6]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[F:46][CH:43]1[CH2:44][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[C:3]=3[CH:4]=[C:5]2[C:11]2[N:16]=[C:15]([C:17]3[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:39])=[O:40])=[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=2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 90333458HCID 90333458, compound

Product 1

HCID 90341041HCID 90341041, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(6-(4-fluoro-1H-indol-2-yl)-5-(1-fluoro-2-hydroxyethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (465 mg, 0.717 mmol) and triphenylphosphine (282 mg, 1.075 mmol) in DCM (15 mL) was added diisopropyl azodicarboxylate (217 mg, 1.075 mmol). The resulting mixture was stirred at RT overnight and concentrated in vacuo. The resulting residue was purified using column chromatography (eluted with 20-50% ethyl acetate/hexane) to provide 5-(5,11-difluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (250 mg, yield: 55%). MS (M+H)+: 631.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified
  3. washcolumn chromatography (eluted with 20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95c6e94668d841d8af18fe0f1d0c6f05
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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