2-Iodoxybenzoic acid → HCID 86719345, compound

HRID 922372Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:27][OH:28])=[N:16][C:17]=1[N:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I(C1C=CC=CC=1C(O)=O)(=O)=O>ClCCCl>[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:27]=[O:28])=[N:16][C:17]=1[N:18]1[CH2:23][CH2:22][N:21]([CH:24]([CH3:25])[CH3:26])[CH2:20][CH2:19]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-isopropylpiperazin-1-yl)pyridin-2-yl)methanol (1.07 g, 2.61 mmol) in 1,2-dichloroethane (20 mL) under nitrogen was added 2-iodoxybenzoic acid (0.88 g, 3.14 mmol) at rt. The reaction mixture was stirred at 80° C. for 1.5 h. After that time the reaction was cooled to rt and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 95:5 dichloromethane/methanol) to give 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-isopropylpiperazin-1-yl)picolinaldehyde (0.63 g, 59%) as a brown solid: 1H NMR (400 MHz, CDCl3): δ 9.85 (s, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H), 4.19-4.15 (m, 2H), 4.02-3.88 (m, 6H), 3.56-3.48 (m, 1H), 3.20 (br s, 4H), 1.37 (d, J=6.4 Hz, 6H), 0.90 (s, 9H), 0.09 (s, 6H); ESI MS m/z 408 [M+H]+.

Workup

temperatureAfter that time the reaction was cooled to rt
concentrationconcentrated under reduced pressure
customThe product was purified by flash column chromatography (silica gel, 95:5 dichloromethane/methanol)

Sources & evidence

ORD record: ord-b0a73585b15f4ed5b45d5fef147d9f2b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278940B2

Reaction notes

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