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

HRID 1929097Notes

Reaction equation

[F:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6]([CH2:9][OH:10])=[CH:7][O:8][C:4]=2[CH:3]=1.[CH3:13][CH2:14][O:15][C:16]([C:18]1[N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:20]2[C:25]([CH:26]=1)=[C:24](O)[CH:23]=[CH:22][CH:21]=2)=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C.N(C(OCC)=O)=NC([O-])=O>C1COCC1>[CH3:13][CH2:14][O:15][C:16]([C:18]1[N:19]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:20]2[C:25]([CH:26]=1)=[C:24]([O:10][CH2:9][C:6]1[C:5]3[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=3[O:8][CH:7]=1)[CH:23]=[CH:22][CH:21]=2)=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

additionaddition the mixture
customThen the mixture is evaporated under reduced pressure
additionThe residue is diluted with ethyl acetate
washwashed sat. NaHCO3- and NaCl-solution
dry with materialdried over Na2SO4
customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel)

Sources & evidence

ORD record: ord-9b43a907e3854c10a2e16fbedc378a77
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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