Hexane → 3-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl ester

HRID 1394624Notes

Reaction equation

HRID 1394624 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[C:13](Br)[CH:12]=[CH:11][CH:10]=2)[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+].CCCCCC>C1(C)C=CC=CC=1.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.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH:4]=[C:5]([C:7]1[N:8]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:9]2[C:14]([CH:15]=1)=[C:13]([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])[CH:12]=[CH:11][CH:10]=2)[CH3:6]

Participants

9

Reactant 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 17952696(2-Butoxy-3,5-diisopropylphenyl)-boronic acidHCID 692210343-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl ester

Product 1

HCID 692207963-[1-Benzenesulfonyl-4-(2-butoxy-3,5-diisopropyl-phenyl)-1H-indol-2-yl]-but-2-enoic acid methyl esterYield 48%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
75 °C

Procedure

3-(1-Benzenesulfonyl-4-bromo-1H-indol-2-yl)-but-2-enoic acid methyl ester (117 mg, 0.27 mmol) and 2-butoxy-3,5-diisopropylphenyl-boronic acid (150 mg, 54 mmol) (see Example 17, step B) were dissolved in toluene (2 mL) under a nitrogen atmosphere. Tetrakis(triphenylphosphine) palladium (31 mg, 0.027 mmol) and 2N Na2CO3 (0.7 mL) were added and the biphasic mixture stirred at 75° C. for 16 h. The reaction was diluted with water/ethyl acetate. The layers were separated and the aqueous layer was washed with ethyl acetate. The organic portions were passed through a pad of Celite, dried (MgSO4), filtered and concentrated in vacuo to provide 243 mg of a crude black oil. Radial chromatography using (99:1) hexane:ethyl acetate provided 76 mg (48%) of product. 1H NMR (250 MHz, CDCl3): δ 8.15 (d, 1H, 8.2), 7.66 (m, 2H), 7.46-7.27 (m, 5H), 7.11 (d, 1H, J=2.2), 6.90 (d, 1H, J=2.2), 6.54 (s, 1H), 6.05 (d, 1H, J=1.2), 3.80 (s, 3H), 3.36 (sep, 1H, J=6.9), 3.04 (t, 2H, J=6.0), 2.88 (sep, 1H, J=6.9), 2.61 (d, 3H, J=1.2), 1.25 (d, 6H, J=6.9), 1.24 (d, 6H, J=6.9), 1.08-0.87 (m, 4H), 0.62 (t, 3H, J=7.0). MS [EI+] 588 (M+H)+ [EI−] 586 (M−H)+.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide 243 mg of a crude black oil

Sources & evidence

ORD record
ord-c440ffa8c5b648f88785f773496bbb4f
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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