Potassium tert-butoxide → HCID 86643471, compound

HRID 1894735Notes

Reaction equation

HRID 1894735 reaction equation
[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][C:9]([C@H:13]4[C@@H:17]([C:18]5[C:26]6[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=6)[NH:20][CH:19]=5)[C:16](=[O:27])[NH:15][C:14]4=[O:28])=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.CC(C)([O-])C.[K+]>O1CCCC1>[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][C:9]([C@H:13]4[C@H:17]([C:18]5[C:26]6[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=6)[NH:20][CH:19]=5)[C:16](=[O:27])[NH:15][C:14]4=[O:28])=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59409001HCID 59409001, compound

Product 1

HCID 86643471HCID 86643471, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione (760 mg, 2.06 mmol) in anhydrous tetrahydrofuran (10 ml) at room temperature was treated with potassium tert-butoxide (1.0 ml, 1.00 mmol; 1M solution in tetrahydrofuran) then heated to 50° C. and stirred for a further 1 hour. The reaction was quenched with water (10 ml) and acidified with 2M hydrochloric acid, and the mixture extracted with dichloromethane (3×50 ml). The combined organic extracts were dried over anhydrous sulfate and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, 1% to 10% methanol in dichloromethane) to provide (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione as an orange solid (46 mg). M.p=141-145° C.; 400 MHz 1H NMR (CDCl3) δ: 8.12 (s, 1H), 8.05 (s, 1H), 7.40 (d, J=8.2 Hz, 1H), 7.29 (s, 1H), 7.23 (m, 1H), 7.11 (m, 2H), 6.78 (s, 1H), 6.39 (d, J=2.7 Hz, 1H), 4.48 (d, J=5.9 Hz, 1H), 4.32 (d, J=5.5 Hz, 1H), 4.16 (t, J=5.5 Hz, 2H), 2.98 (t, J=6.3 Hz, 2H), 2.25 (t, J=6.3 Hz, 2H); LCMS: 370 [M+H].

Workup

  1. customThe reaction was quenched with water (10 ml)
  2. extractionthe mixture extracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organic extracts were dried over anhydrous sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by flash column chromatography (SiO2, 1% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1ca86d9d75c6426684cf29b5e9deb92b
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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