Dichloromethane → (4-(1H-indol-5-yloxy)pyridin-2-yl)methanol

HRID 45170

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([O:19][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of (4-chloropyridin-2-yl)methanol (384 mg, 2.67 mmol) in DMF (12 mL) is added 1H-indol-5-ol (534 mg, 4.01 mmol), and cesium carbonate (1307 mg, 4.01 mmol). The reaction is sealed and heated to 160° C. via microwave irradiation for 30 min. The reaction mixture is then cooled to room temperature and diluted brine and DCM. The resulting layers are separated and the aqueous layer is extracted three additional times with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated. The resulting residue is purified via FCC (0-100% EtOAc/heptane) to give the title compound. MS (ESI) m/z 241.2 (M+1).

Workup

customThe reaction is sealed
temperatureThe reaction mixture is then cooled to room temperature
customThe resulting layers are separated
extractionthe aqueous layer is extracted three additional times with DCM
dry with materialThe organic layers are combined dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue is purified via FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record: ord-18a89f39b45340c89b5f4b56d8d35732
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541432B2

Linked notes

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