Nitrogen → Abt-116

HRID 2410076Notes

Reaction equation

[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][C:5]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:6]=1[CH2:7][NH:8][C:9]([NH2:11])=[O:10].C(Cl)(Cl)Cl.C[C:27]1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)O[C:29]2[C:30](P(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:31][CH:32]=[CH:33][C:28]1=2.[C:68]([O-])([O-])=O.[Cs+].[Cs+].[N:74]#[N:75]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][C:5]1[CH:15]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:13]=[CH:12][C:6]=1[CH2:7][NH:8][C:9]([NH:11][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]2[C:28]=1[CH:27]=[N:74][N:75]2[CH3:68])=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of Example 3A (5.12 g, 16.9 mmol), Example 2C (3.78 g, 17.9 mmol), Pd2 dba3:CHCl3 (264 mg, 0.255 mmol), xantphos (442 mg, 0.764 mmol), and Cs2CO3 (8.28 g, 25.4 mmol) in dioxane (60 mL) was flushed with N2 and stirred at 90° C. for 16 hours. The mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed sequentially with water and brine, and purified by flash chromatography (0 to 35% ethyl acetate/dichloromethane) to provide the title compound. 1H-NMR (DMSO-d6) δ 8.82 (s, 1H), 8.05 (s, 1H), 7.64 (d, 1H), 7.50-7.53 (m, 3H), 7.20 (t, 1H), 7.14 (d, 1H), 6.81 (t, 1H), 4.45 (d, 2H), 4.00 (s, 3H), 2.70 (ddd, 2H), 1.45 (ddd, 2H), 0.97 (s, 9H).

Workup

concentrationThe mixture was concentrated under reduced pressure
additiondiluted with ethyl acetate
washwashed sequentially with water and brine
custompurified by flash chromatography (0 to 35% ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-9f8551f0f8b647a295c291568c412923
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815930B2

Reaction notes

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