Potassium Carbonate → 3-cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid methyl ester

HRID 2217771Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([NH2:11])[CH:5]=1.[CH:13]1([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[C:26]([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Fe+2].CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([C:18]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:11]2[CH3:26])=[CH:8][CH:9]=1)=[O:12]

Participants

Conditions

Temperature: 130 °C

Procedure

A 100 mL three neck flask equipped with a thermocouple, condenser and stir bar was purged with argon. 3-Amino-4-chlorobenzoic acid methyl ester (5.0 g, 26.94 mmol), 2-cyclopentylethynyl-pyridine (5.528 g, 32.33 mmol), Pd(OAc)2 (181 mg, 0.81 mmol), DtBPF (767 mg, 1.62 mmol), K2CO3 (9.29 g, 67.35 mmol) and NMP (25 mL) were then charged. The reaction was heated to 130° C. and monitored by HPLC. The reaction was complete after 6 hours.

Workup

customwas purged with argon

Sources & evidence

ORD record: ord-317eb09d561540c498635d25d42fc5a2
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408076B2

Reaction notes

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