Triethylamine → HCID 57721351, compound

HRID 1986100Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15]2.C(N(CC)CC)C>CC#N>[Cl:1][C:2]1[C:3]([C:4]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

Conditions

Temperature: 23 °C

Procedure

2-Chloronicotinoyl chloride (200 mg, 1.14 mmol) was dissolved in CH3CN (5.6 mL). 5-Fluoroindoline (171 mg, 1.25 mmol) was added followed by triethylamine (0.24 mL, 1.71 mmol) and the reaction mixture was stirred at 23° C. for 16 h. The solvent was removed by evaporation and the residue was partitioned between CH2Cl2 (10 mL) and sat. aq. NaHCO3 solution (10 mL). The organic phase was removed and the aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo. Flash column chromatography (40 g SiO2, 2% CH3OH—CH2Cl2) afforded the desired product as an off-white solid (247.8 mg, 79%). 1H NMR (DMSO-d6) δ 3.14 (t, 2H, J=8.39 Hz), 3.82 (t, 2H, J=8.39 Hz), 7.09 (dt, 1H, J=9.03, 2.80 Hz,), 7.20 (dd, 1H, J=8.39, 2.80 Hz), 7.60 (dd, 1H, J=7.38, 4.83 Hz), 8.10 (dd, 1H, J=7.63, 2.03 Hz), 8.15 (dd, 1H, J=8.90, 4.83 Hz), 8.55 (dd, 1H, J=4.83, 1.78 Hz).

Workup

customThe solvent was removed by evaporation
customthe residue was partitioned between CH2Cl2 (10 mL) and sat. aq. NaHCO3 solution (10 mL)
customThe organic phase was removed
extractionthe aqueous phase was extracted with CH2Cl2 (2×10 mL)
dry with materialThe combined organics were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-66a7473c31fb4b9d967df3693269e3ee
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547782B2

Reaction notes

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