Potassium Phosphate, Tribasic → (E)-ethyl 3-(5-chloropent-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

HRID 533278Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[Cl:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]/B1OC(C)(C)C(C)(C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O[Pd]OC(=O)C)(=O)C>[Cl:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]/[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 3-bromo-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (The synthesis of this compound was described in EXAMPLE 134B as an intermediate) (404 mg), (E)-2-(5-chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.394 ml), diacetoxypalladium (19.28 mg), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (70.5 mg) and K3PO4 (547 mg) was heated in a microwave reactor (CEM Discover) at 100° C. for 1 hour. The insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with dichloromethane to provide the title compound.

Workup

customThe synthesis of this compound
customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated
customThe residue was purified by flash chromatography
washeluting with dichloromethane

Sources & evidence

ORD record: ord-7ebb30a835e04004a1aa260f62bb0acc
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853209B2

Reaction notes

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