Potassium Carbonate → HCID 136158594, compound

HRID 853662Notes

Reaction equation

HRID 853662 reaction equation
C(OC(=O)[O:5][C:6]1[C:15]2[N:14]=[CH:13][CH:12]=[N:11][C:10]=2[C:9]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]2[C:30](=[O:42])[N:31]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[C:32](=[O:33])[C:7]=12)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C1C=CN=CC=1)C.O>[CH:17]([O:16][C:9]1[C:10]2[N:11]=[CH:12][CH:13]=[N:14][C:15]=2[C:6]([OH:5])=[C:7]2[C:32](=[O:33])[N:31]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[C:30](=[O:42])[C:8]=12)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 58928679HCID 58928679, compound

Product 1

HCID 136158594HCID 136158594, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoxalin-5-yl ester ethyl ester 244 (500 mg, 0.87 mmol) was dissolved in THF (9 mL, 0.1 M) along with DMAP (211 mg, 1.73 mmol, 2 equiv.). A solution of K2CO3 (1.20 g, 8.66 mmol, and 10 equiv.) was dissolved separately in H2O (6 mL) before being transferred to the reaction mixture. The reaction was allowed to stir for 18 hours and quenched with HCl (20 mL, 1 N) and extracted with ethyl acetate (2×30 mL). The organic layer was washed with saturated NH4Cl solution (25 mL), brine solution (25 mL) and dried over Na2SO4 and concentrated in vacuo to yield 5-benzhydryloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoxaline-6,8-dione 245 (94%, 413 mg, 0.82 mmol). 1H NMR (300 MHz) CDCl3 δ 9.08 (d, J=1.5 Hz, 1 H), 8.92 (d, J=1.5 Hz, 1H), 7.67 (s, 1 H), 7.67-7.42 (dd, J1=1.5 Hz, J2=8.4 Hz, 4 H), 7.43-7.48 (m, 2 H), 7.19-7.27 (m, 7 H), 7.03-7.20 (m, 1 H), 4.86 (s, 2 H). MS: 528.0 (M+23). TLC Rf: 0.2 Hexanes/Ethyl acetate (8/2)

Workup

  1. customquenched with HCl (20 mL, 1 N)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe organic layer was washed with saturated NH4Cl solution (25 mL), brine solution (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-025bb5394cb1423684622e258e8e4791
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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