Sodium Carbonate → 3-[1-Benzenesulfonyl-3-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl ester

HRID 1394617Notes

Reaction equation

HRID 1394617 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]=[C:10]2I)[CH3:6].[CH2:27]([O:31][C:32]1[C:37]([CH:38]([CH3:40])[CH3:39])=[CH:36][C:35]([CH:41]([CH3:43])[CH3:42])=[CH:34][C:33]=1B(O)O)[CH2:28][CH2:29][CH3:30].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCCCCC.O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:11]=[C:10]2[C:33]1[CH:34]=[C:35]([CH:41]([CH3:43])[CH3:42])[CH:36]=[C:37]([CH:38]([CH3:39])[CH3:40])[C:32]=1[O:31][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:6]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 692188963-(1-Benzenesulfonyl-3-iodo-1H-indol-5-yl)-but-2-enoic acid methyl ester

Product 1

HCID 692206043-[1-Benzenesulfonyl-3-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-5-yl]-but-2-enoic acid methyl esterYield 151.2%

Reagents, catalysts & solvents 5

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

3-(1-Benzenesulfonyl-3-iodo-1H-indol-5-yl)-but-2-enoic acid methyl ester (653 mg, 1.35 mmol) and (2-butoxy-3,5-diisopropylphenyl)-boronic acid (415 mg, 1.49 mmol) were dissolved in toluene (8 mL) under a nitrogen atmosphere. Tetrakis(triphenylphosphine) palladium (172 mg, 0.15 mmol) and 2N Na2CO3 (2.7 mL) was added and the biphasic mixture stirred at 80° C. for 6 h. The reaction was judged complete by TLC (9:1) in hexane:ethyl acetate but was allowed to stir overnight at room temperature. The reaction was diluted with water (5 mL)/ethyl acetate (15 mL). The layers were separated and the aqueous washed with ethyl acetate (10 mL). The organic portions were passed through a pad of Celite, dried (MgSO4), filtered and concentrated in vacuo to provide 1.20 g of a dark brown oil. Chromatography (SiO2, hexanes/ethyl acetate) provided 294 mg (37%) of a yellow foam. 1H NMR (250 MHz, CDCl3): δ 8.06 (d, 1H, J=8.7), 7.94 (m, 2H), 7.80 (s, 1H), 7.75 (d, 1H, J=1.7), 7.56-7.45 (m, 4H), 7.13 (m, 2H), 6.14 (d, 1H, J=1.2), 3.75 (s, 3H), 3.39 (sep, 1H, J=6.9), 3.29 (t, 2H, J=6.3), 2.93 (sep, 1H, J=6.9), 2.60 (d, 3H, J=1.2), 1.29 (d, 7H, J=6.9), 1.27 (d, 7H, J=6.9), 1.22 (m, 2H), 0.62 (t, 3H, J=7.2). MS [EI+] 588 (M+H)+.

Workup

  1. stirringto stir overnight at room temperature
  2. customThe layers were separated
  3. washthe aqueous washed with ethyl acetate (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52fa6a63d4154c339d010de42da5724d
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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