Dimethylformamide → HCID 22047630, compound

HRID 1072989Notes

Reaction equation

[Cl:1][C:2]1[C:7]([OH:8])=[C:6](I)[CH:5]=[C:4]([CH2:10][OH:11])[N:3]=1.[CH2:12]([Si](C)(C)C)[C:13]#[CH:14].N1CCCCC1.CN(C=O)C>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([CH2:10][OH:11])[CH:5]=[C:6]2[CH:12]=[C:13]([CH3:14])[O:8][C:7]=12

Participants

Conditions

Temperature: 45 °C

Procedure

2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol (C2) (4.6 g, 16 mmol), propargyl trimethylsilane (2 g, 17.8 mmol), bis(triphenylphosphine)palladium dichloride (156 mg, 0.21 mmol), cuprous iodide (122 mg, 0.64 mmol), and piperidine (3.52 mL, 26.6 mmol) are added to 25 mL DMF in a dry flask under N2. The mixture is warmed to 45° C. for 7 h, is stirred overnight at rt, and is diluted with 150 mL EtOAc. The mixture is washed with 4×50 mL 50% saturated 1:1 NaCl/NaHCO3. The organic layer is dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo to an amber oil. The crude material is chromatographed over 40 g silica gel (230-400 mesh) eluting with 35% EtOAc/hexane to afford (7-chloro-2-methylfuro[2,3-c]pyridin-5-yl)methanol (C24) (44% yield). MS (CI) for C9H8ClNO2, m/z: 198 (M+H).

Workup

washThe mixture is washed with 4×50 mL 50% saturated 1:1 NaCl/NaHCO3
dry with materialThe organic layer is dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo to an amber oil
customThe crude material is chromatographed over 40 g silica gel (230-400 mesh)
washeluting with 35% EtOAc/hexane

Sources & evidence

ORD record: ord-468a0cd0881a4c30add5e591ece8a179
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06911543B2

Reaction notes

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