Potassium Phosphate, Tribasic → ethyl 3-(3-(naphthalen-1-yloxy)propyl)-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylate

HRID 576290Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.[CH3:30][N:31]1[C:35]([CH3:36])=[C:34](B2OC(C)(C)C(C)(C)O2)[C:33]([CH3:46])=[N:32]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(O[Pd]OC(=O)C)(=O)C>[C:20]1([O:19][CH2:18][CH2:17][CH2:16][C:7]2[C:6]3[C:10](=[C:2]([C:34]4[C:33]([CH3:46])=[N:32][N:31]([CH3:30])[C:35]=4[CH3:36])[CH:3]=[CH:4][CH:5]=3)[NH:9][C:8]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (1.605 g) and 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.838 g) in toluene (25 ml) was added diacetoxypalladium (0.080 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.291 g), and K3PO4 (2.259 g). The resulting mixture was stirred at 110° C. overnight. Silica gel (25 g) was added and the mixture was carefully dried on house vacumn overnight. The gel powder was loaded onto a flash column and eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound.

Workup

additionSilica gel (25 g) was added
customthe mixture was carefully dried on house vacumn overnight
washeluted with 0-50% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-20c57659340e42dfa224f71a6da16b30
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035047B2

Reaction notes

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