Water → HCID 58928738, compound

HRID 853622Notes

Reaction equation

HRID 853622 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([OH:32])[C:9]=3[C:8]2=[O:33])=[CH:4][CH:3]=1.[C:36]([O-])([O-])=O.[K+].[K+].CI.O>C(#N)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:25])[CH3:24])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:32][CH3:36])[C:9]=3[C:8]2=[O:33])=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1361585867-(4-Fluoro-benzyl)-5-hydroxy-9-triisopropylsilanyloxy-pyrrolo[3,4-g]quinoline-6,8-dione

Product 1

HCID 58928738HCID 58928738, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12 from the monosilylation reaction was heated at 40° C. in anhydrous acetonitrile with K2CO3 (1.64 g, 11.8 mmol) and methyl iodide (4.2 g, 29.6 mmol) for 5 hours. The reaction mixture was worked up by addition of H2O and EtOAc. The organic layer was washed with H2O and the solvent was removed in vacuo. The residue was purified by column chromatography using a gradient of 10% EtOAc-Hex to elute the product 13 as a yellow solid (72% for two steps). 1H NMR (300 MHz, CDCl3) δ 1.13 (d, 18H, J=8 Hz), 1.53 (septet, 3H, J=7 Hz), 4.29 (s, 3H), 4.84 (s, 2H), 7.00 (t, 2H, J=8 Hz), 7.48 (dd, 2H, J=5, 8 Hz), 7.58 (dd, 1H, J=4, 8 Hz), 8.65 (dd, 1H, J=2, 8 Hz), 8.93 (dd, 1H, J=2, 4 Hz); EI MS (m/z) 509.7 [MH+], 531.4 [M+Na].

Workup

  1. customfrom the monosilylation reaction
  2. washThe organic layer was washed with H2O
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography
  5. washto elute the product 13 as a yellow solid (72% for two steps)

Sources & evidence

ORD record
ord-fc1512a069834475b513cc93d7c1b3ea
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…