Triphenylphosphine → 1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1715222Notes

Reaction equation

HRID 1715222 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[C:33]1[C:34]([C:42]2([CH2:57][OH:58])[C:50]3[C:45](=[N:46][CH:47]=[CH:48][CH:49]=3)[N:44]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:43]2=[O:56])=[CH:35][C:36]2[O:40][CH2:39][O:38][C:37]=2[CH:41]=1>C1COCC1>[CH2:51]([N:44]1[C:45]2=[N:46][CH:47]=[CH:48][CH:49]=[C:50]2[C:42]2([C:34]3=[CH:35][C:36]4[O:40][CH2:39][O:38][C:37]=4[CH:41]=[C:33]3[O:58][CH2:57]2)[C:43]1=[O:56])[CH2:52][CH2:53][CH2:54][CH3:55]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 119628123-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 118483031'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of triphenylphosphine (2.61 g, 9.95 mmol) and diethyl azodicarboxylate (1.73 g, 9.95 mmol) in anhydrous THF (100 mL) was added slowly a solution of 3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (2.85 g, 7.69 mmol) in anhydrous THF (50.0 mL) at 0° C. The brown reaction solution was stirred at ambient temperature for 16 h and quenched with saturated ammonium chloride (50.0 mL). The organic solvent was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (100 mL). The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to give the title compound (1.45 g, 54%), which was triturated from ether and hexane to give a colorless solid: mp 126-127° C.; 1H NMR (300 MHz, CDCl3) δ 8.18 (dd, 1H), 7.54 (dd, 1H), 7.01 (dd, 1H), 6.666 (s, 1H), 6.25 (s, 1H), 5.89 (d, 1H), 4.71 (ABq, 2H), 3.68 (t, 2H), 1.70-1.60 (m, 2H), 1.32-1.22 (m, 4H), 0.82 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.9, 156.8, 156.0, 149.0, 147.9, 142.3, 132.0, 126.7, 119.3, 119.2, 103.4, 101.9, 93.8, 79.7, 57.4, 39.3, 28.9, 27.1, 22.2, 14.3; MS (ES+, m/z) 353 (M+1).

Workup

  1. customquenched with saturated ammonium chloride (50.0 mL)
  2. customThe organic solvent was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-bef4b5b9c8ae4a73bbd37709b534ac92
Source dataset
uspto-grants-2010_09
Patent number
US07799798B2

Reaction notes

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