Allyl bromide → 5-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853619Notes

Reaction equation

HRID 853619 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([OH:25])[C:9]=3[C:8]2=[O:26])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:35](Br)[CH:36]=[CH2:37]>CN(C)C=O.C(OC(=O)C)C>[CH2:37]([O:25][C:10]1[C:9]2[C:8](=[O:26])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:28][CH:27]=3)[C:19](=[O:20])[C:18]=2[C:17]([O:21][CH2:22][O:23][CH3:24])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2)[CH:36]=[CH2:35]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1361585857-(4-Fluoro-benzyl)-5-hydroxy-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

Product 1

HCID 589289585-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methoxymethyl ether 6 (0.0172 g, 0.045 mmol) was dissolved in 1.5 mL dry dimethylformamide (DMF). Ground K2CO3 (0.0186 g, 0.135 mmol) was added, followed by allyl bromide (0.0077 mL, 0.09 mmol). The mixture was stirred at room temperature overnight, then diluted with 100 mL of ethylacetate, washed with saturated NH4Cl solution, dried (MgSO4), and concentrated to give crude 10. The crude product 10 was chromatographed on silica gel, eluting with ethylacetate and hexanes to give white solid allyl, methoxymethyl diether 10: (0.0063 g, 33%). 1H NMR (CDCl3) δ 9.1 (dd, 1H), 8.8 (dd, 1H), 7.6 (dd, 1H), 7.5 (dd, 2H), 7.0 (t, 2H), 6.1 (m, 1H), 5.8 (s, 2H),5.5 (d, 1H), 5.3 (d, 1H), 5.1 (d, 2H), 4.8 (s, 2H). MS: 423 (M+1); 445 (M+23).

Workup

  1. washwashed with saturated NH4Cl solution
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give crude 10
  5. customThe crude product 10 was chromatographed on silica gel
  6. washeluting with ethylacetate and hexanes

Sources & evidence

ORD record
ord-01b95bb27be54ee9bf7c1f77e1854f7f
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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