Potassium Carbonate → HCID 11354054, compound

HRID 1602369Notes

Reaction equation

HRID 1602369 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.Br/[C:18](=[CH:26]\[C:27]1[C:35]2[C:30](=[CH:31][C:32]([Cl:37])=[CH:33][C:34]=2[Cl:36])[N:29]([S:38]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)(=[O:40])=[O:39])[C:28]=1[C:48]([O:50][CH2:51][CH3:52])=[O:49])/[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[S:53]1[CH:57]=[CH:56][C:55](B(O)O)=[CH:54]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1CCCCC1.C1CCCCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:53]1[CH:57]=[CH:56][C:55](/[C:18](=[CH:26]\[C:27]2[C:35]3[C:30](=[CH:31][C:32]([Cl:37])=[CH:33][C:34]=3[Cl:36])[N:29]([S:38]([C:41]3[CH:42]=[CH:43][C:44]([CH3:47])=[CH:45][CH:46]=3)(=[O:40])=[O:39])[C:28]=2[C:48]([O:50][CH2:51][CH3:52])=[O:49])/[C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[CH:54]1

Participants

9

Reactant 4

HCID 11430Potassium Carbonate2×HCID 521585Tris(furan-2-yl)phosphane2×HCID 581760Thiophene-3-boronic acid2×HCID 11157837HCID 11157837, compound

Product 1

HCID 11354054HCID 11354054, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolventHCID 21895417Cyclohexane diethyletherSolvent

Conditions

Temperature
60 °C

Procedure

Combine tris(dibenzylideneacetone)dipalladium(0) (204 mg, 0.223 mmol) and tri-(fur-2-yl)phosphine (413 mg, 1.78 mmol) in tetrahydrofuran (60 mL). After 5 minutes, add (Z)-2-bromo-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester (1.85 g, 3.0 mmol), thiophene-3-boronic acid (1.16 g, 9.1 mmol), and powdered potassium carbonate (1.27 g, 9.2 mmol). Heat to 60° C. After 6 days, add thiophene-3-boronic acid (744 mg, 5.8 mmol), tri-(fur-2-yl)phosphine (206 mg, 0.887 mmol), tris(dibenzylideneacetone)dipalladium(0) (102 mg, 0.111 mmol), and powdered Potassium carbonate (800 mg, 5.80 mmol). After 3 more days, dilute the reaction mixture with cyclohexane (60 mL) and chromatograph on silica gel eluting with 3/1 cyclohexane/ether to give the title compound. 1H NMR (CDCl3) δ 7.94 (d, 1H, J=1.7 Hz), 7.74 (d, 2H, J=8.4 Hz), 7.72 (s, 1H), 7.26 (d, 2H, J=8.0 Hz), 7.24 (d, 1H, J=1.7 Hz), 7.03 (d, 1H, J=4.4 Hz), 7.02 (d, 1H, J=1.5 Hz), 6.77 (dd, 1H, J=4.7, 1.6 Hz), 4.20 (q, 2H, J=7.15 Hz), 2.40 (s, 3H), 1.55 (s, 9H), 1.28 (t, 3H, J=7.15 Hz).

Workup

  1. waitAfter 6 days

Sources & evidence

ORD record
ord-6fb51decdbc34c45ab6c7a08077c365a
Source dataset
uspto-grants-1999_11
Patent number
US05981553

Reaction notes

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