Triphenylphosphine → 4-(6-Fluoro-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-tert-butyl 2-ethyl 4-hydroxy-1H-indole-1,2-dicarboxylate	HCID 59600138	—
Reactant	(6-Fluorobenzofuran-3-YL)methanol	HCID 66841405	—
Reactant	N-ethoxycarbonyliminocarbamate	HCID 86599450	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-(6-Fluoro-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester	HCID 66841657	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

111 (2 g, 12 mmol), 102 (3.7 g, 12 mmol), triphenylphosphine (9.4 g, 36.1 mmol) and DIPEA (6.2 ml, 36.1 mmol) are dissolved in 50 ml of THF and cooled to 0° C. Then 40% ethyl azodicarboxylate solution in THF (15.7 ml, 36.1 mmol) is added dropwise. After completed addition the mixture is stirred for 16 h (TLC control) at rt. Then the mixture is evaporated under reduced pressure. The residue is diluted with ethyl acetate, washed sat. NaHCO3- and NaCl-solution, and dried over Na2SO4. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07858781B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-b3d8dab059c64fceb69f363c1557e88d
Source note	uspto-grants-2010_12