Ethyl Acetate → HCID 178494856, compound

HRID 452984Notes

Reaction equation

HRID 452984 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:3]=1[C:4](/[N:6]=[C:7]1/[N:8]([CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][O:19]2)[N:9]([CH3:16])[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:11]/1)=[O:5].[CH3:31][O:32][CH2:33]/[CH:34]=[CH:35]/B1OC(C)(C)C(C)(C)O1.[F-].[Cs+].C(OCC)(=O)C>C(COC)OC.CO>[C:12]([C:10]1[N:9]([CH3:16])[N:8]([CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][O:19]2)/[C:7](=[N:6]/[C:4](=[O:5])[C:3]2[CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=[CH:26][C:2]=2/[CH:35]=[CH:34]/[CH2:33][O:32][CH3:31])/[CH:11]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178480265HCID 178480265, compound

Product 1

HCID 178494856HCID 178494856, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of Example 88 (146 mg, 0.299 mmol) and (E)-2-(3-methoxyprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (148 mg, 0.747 mmol) in dimethoxyethane (1 mL) and methanol (0.5 mL) was added palladium tetrakistriphenyl phosphine (86 mg, 0.075 mmol) and cesium fluoride (159 mg, 1.05 mmol). This mixture was microwaved at 100° C. for 10 minutes. To the reaction was added ethyl acetate and the mixture was filtered through celite and purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% solvent A in hexanes, solvent A: 10% MeOH in ethyl acetate) to afford the title compound (74 mg, 52%). 1H NMR (300 MHz, CDCl3) δ ppm 1.44 (s, 9H) 1.71-1.85 (m, 3 H) 1.98-2.07 (m, 1H) 3.37 (s, 3H) 3.69-3.82 (m, 2H) 3.88 (s, 3H) 4.11-4.13 (m, 2H) 4.18-4.32 (m, 2H) 4.48-4.58 (m, 1H) 6.22 (dt, J=15.96, 6.30 Hz, 1H) 7.03 (s, 1H) 7.46-7.53 (m, 1H) 7.57-7.65 (m, 2H) 8.20 (s, 1H); MS (DCI/NH3) m/z 480 (M+H)+.

Workup

  1. customThis mixture was microwaved at 100° C. for 10 minutes
  2. filtrationthe mixture was filtered through celite
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-cd2b7b46fd5a41faadbe981ee7106528
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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