ChemicalBook CAS DataBase List P7C3-A20

P7C3-A20 synthesis

10synthesis methods

Product Name:P7C3-A20
CAS Number:1235481-90-9
Molecular formula:C22H19Br2FN2O
Molecular Weight:506.21

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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1235481-90-9
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Yield: 88%

Reaction Conditions:

with mercaptoacetic acid;lithium hydroxide in N,N-dimethyl-formamide at 20; for 1 h;

Steps:

6a.5 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

To a vial containing N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (21.0 mg, 0.030 mmol; see representative procedure 4) was added lithium hydroxide (3.2 mg, 0.134 mmol), dimethylformamide (0.5 ml, 0.06 M) and mercaptoacetic acid (4.2 ul 0.060 mmol).
After stirring at rt for 1 h the reaction mixture was diluted with EtOAc and washed sequentially with water, saturated sodium bicarbonate solution, water (3*) and brine.
The organic layer was dried over Na₂SO₄, filtered and condensed.
The crude reaction mixture was purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg isolated. Yield=88% Additional Representative Procedure (1370) DAST [(Et₂NSF₃) 0.12 ml, 0.916 mmol] was added dropwise to a solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (0.102 g, 0.203 mmol) in 6.0 ml of anhydrous DCM at -78° C. The reaction was stirred at -78° C. for one hour before being slowly warmed to 0° C. over 5 hours. The reaction was quenched by addition of phosphate buffer (pH=8) and extracted with DCM. The aqueous phase was extracted twice with 10 ml DCM. The combined organics were dried over Na₂SO₄, filtered and concentrated. The crude reaction material was purified by flash chromatography on Si02 (20% EtOAc/hexanes/0.2% TEA). Fractions containing the desired fluorinated product were further purified with 40% EtOAc/hexanes (+0.1% TEA). Isolated 5.7 mg desired product. Analytical Data for the Title Compound of Example 6a (1371) ¹H NMR (CDCl₃, 500 MHz) ζ 8.16 (2H, J=2.0 Hz), 7.56 (dd, 2H, J=1.9, 8.7 Hz), 7.31 (d, 2H, J=8.6 Hz), 7.11 (t, 1H, J=8.1 Hz), 6.36 (dd, 1H, J=2.2, 8.1 Hz), 6.23 (dd, 1H, J=2.0, 8.0 Hz), 6.15 (t, 1H, J=2.3 Hz), 5.11 (dddd, 1H, J=4.6, 5.8, 10.4, 47.7 Hz), 4.60 (m, 2H), 4.39 (dm, 2H), 3.95 (t, 1H, J=6.3 Hz), 3.75 (s, 3H) (1372) MS (ESI), m/z: 504.9 (M+1)⁺. ([M+1]+ for C₂₂H₁₉Br₂FN₂O calculated 505.0)

References:

Board of Regents of The University of Texas System;McKnight, Steven L.;Pieper, Andrew A.;Ready, Joseph M.;De Brabander, Jef K. US9095571, 2015, B2 Location in patent:Page/Page column 97; 98