1,2-Dimethoxyethane → HCID 21865173, compound

HRID 859028Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[N:16]3)=[CH:11][CH:10]=2)[CH:3]=1.CO[CH2:21][CH2:22]OC.C(=O)([O-])[O-].[Na+].[Na+]>[OH-].[Na+]>[N:5]1[CH:22]=[CH:21][CH:2]=[C:3]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][CH:10]=3)[CH:3]=2)[CH:4]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a 5 mL, microwave vial containing 7-(6-chloro-pyrimidin-4-yloxy)-quinoline, (Example 102(a)), (0.30 g, 1.2 mmol) and ethylene glycol dimethyl ether (2 mL) was added 3-diethyl (3-pyridyl)borane (0.21 g, 1.5 mmol, Aldrich), 1 N sodium carbonate (1.8 mL), and palladium(0)-tetrakis-triphenylphosphine (0.14 g, 0.15 mmol, Strem Chemical). The vial was sealed and heated at 200° C. for 20 min in a microwave synthesizer, allowed to cool to room temperature, and the reaction mixture was diluted with 1 N sodium hydroxide (25 mL) and extracted with dichloromethane (2×50 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated onto silica gel. The crude material was purified by silica gel chromatography (gradient: 1–2% 2 N ammonia in methanol/dichloromethane) to obtain the title compound as an off-white solid. Mp: 155–158° C. MS (ESI, pos. ion.) m/z: 301 (M+1).

Workup

customThe vial was sealed
temperatureto cool to room temperature
extractionextracted with dichloromethane (2×50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated onto silica gel
customThe crude material was purified by silica gel chromatography (gradient: 1–2% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record: ord-9a31100cc0f54a10ba89871cae4b276e
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148221B2

Reaction notes

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