Triethylamine → HCID 22507767, compound

HRID 985729Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1)#[CH:2].I[C:21]1[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=1[NH:23][S:24]([CH3:27])(=[O:26])=[O:25].C(N(CC)CC)C>CN(C=O)C.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>[CH3:27][S:24]([N:23]1[C:22]2[C:21](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:2]=[C:1]1[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 1-ethynyl-4-(3-(4-methylpiperazino)propoxy)benzene (230 mg, 0.89 mmol), 2-iodo-N-(methanesulfonyl)aniline (0.89 mmol, 296 mg), Cul (17 mg, 0.089 mmol), Pd(PPh3)2Cl2 (32 mg, 0.045 mmol) and triethylamine (0.5 mL) in DMF (5 mL) was stirred at 80° C. for overnight. After concentration, water (20 mL) was added and extracted by methlene chloride (3×20 mL). The organics was concentrated and purified by column chromatography afforded the title compound (260 mg): 1H NMR (CDCl3, 400 MHz) δ 8.05 (d, 1H, J=8.8 Hz), 7.55 (d, 1H, J=2.1 Hz), 7.50 (td, 2H, J=8.8,2.1 Hz), 7.32 (d, 1H, J=2.1 Hz), 7.30 (d, 1H, J=2.1 Hz), 6.96 (td, 2H J=2.1, 8.8 Hz), 6.60 (d, 1H, J=0.5 Hz), 4.08 (t, 2H, J=6.3 Hz), 2.74 (s, H), 2.55 (m, 10H), 2.33 (s, 3H), 2.02 (quintet, 2H, J=6.3 Hz); EIMS m/z 462 (M+H+).

Workup

concentrationAfter concentration, water (20 mL)
additionwas added
extractionextracted by methlene chloride (3×20 mL)
concentrationThe organics was concentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-10f5aba7379e4ebfb2acfc5ff712263f
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872834B2

Reaction notes

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