Ethyl diazoacetate → Cyclopropanecarboxylic acid, 2-[1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-5-yl]-, ethyl ester

HRID 269512

Reaction equation

[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:19]=[CH2:20])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N+](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-]>C1(C)C(C)=CC=CC=1>[CH2:28]([O:27][C:25]([CH:24]1[CH2:20][CH:19]1[C:17]1[CH:18]=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:21])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[C:14]2=[N:15][CH:16]=1)=[O:26])[CH3:29]

Participants

Conditions

Temperature: 95 °C

Procedure

1-(Toluene-4-sulfonyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine, (200 mg, 0.67 mmol), and ethyl diazoacetate, (730 μL, 7.0 mmol), were combined in 3 mL xylene and heated to 95° C. for 30 min, then to 115° C. for 4 hours. The solvent was evaporated onder vacuum and the residue purified by silica chromatography, (eluent: methylene chloride), affording 140 mg, (50%), 2-[1-(Toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl ]-cyclopropanecarboxylic acid ethyl ester as a mixture of cis and trans isomers. MS ES+385.3.

Workup

customThe solvent was evaporated onder vacuum
customthe residue purified by silica chromatography, (eluent: methylene chloride),

Sources & evidence

ORD record: ord-f5f3591cadcf49129ce5395bb0b7c2c5
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446199B2

Linked notes

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