Water → HCID 58318599, compound

HRID 473430Notes

Reaction equation

HRID 473430 reaction equation
[CH3:1][C:2]([C:5]1[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22]([CH3:25])(=[O:24])=[O:23])=[N:7][C:8]2[C:13]([CH:14]=1)=[N:12][CH:11]=[C:10]([F:15])[CH:9]=2)(O)C.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O>C1COCC1>[F:15][C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[C:5]([CH:2]([N:30]3[C:26](=[O:36])[C:27]4[C:28](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:29]3=[O:31])[CH3:1])[C:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[S:22]([CH3:25])(=[O:23])=[O:24])=[N:7]2)=[N:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67239005HCID 67239005, compound

Product 1

HCID 58318599HCID 58318599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanol (500 mg, 1.44 mmol) and phthalimide (425 mg, 2.88 mmol) in THF (15 mL) was added triphenylphosphene (757 mg, 2.88 mmol) at 0° C. The reaction mixture was stirred for 10 min at same temperature. Diisopropyl azo-dicarboxylate (0.6 mL, 2.88 mmol) was added to reaction mixture at 0° C. The reaction mixture was stirred for overnight at 0° C. Water was added to reaction mixture and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give 2-(1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1, 5-naphthyridin-3-yl)ethyl) isoindoline-1,3-dione: LC-MS (ESI) m/z 476.0 [M+H]+. It was carried on crude for next step.

Workup

  1. additionwas added triphenylphosphene (757 mg, 2.88 mmol) at 0° C
  2. stirringThe reaction mixture was stirred for overnight at 0° C
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccbcec1b4da34469bd39ced632539421
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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