Benzenesulfonyl chloride → HCID 58361490, compound

HRID 2076446Notes

Reaction equation

HRID 2076446 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C(N(CC)C(C)C)(C)C.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:23]1([S:29]([O:13][C:3]2[C:2]([Br:1])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([CH3:12])=[N:10]3)=[CH:5][CH:4]=2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 136062505HCID 136062505, compound

Product 1

HCID 58361490HCID 58361490, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 8-bromo-2-methylquinolin-7-ol (1.10 g, 4.62 mmol) and N,N-diisopropylethylamine (1.19 g, 9.24 mmol) were dissolved in anhydrous DCM (10 mL), and the solution was cooled to 0° C. Benzenesulfonyl chloride (0.90 g, 5.10 mmol) in 5 mL DCM was added over 10 min, and the reaction mixture was stirred for 14 h at room temperature under argon. Solvent was removed in vacuo, and residue was dissolved in EtOAc and washed twice with saturated aq. NaHCO3 and then dried over anhydrous Na2SO4. Solvent was removed in vacuo, and the residue was purified by SiO2 column chromatography (Hexanes/EtOAc=1/1) to yield SO185 as a white solid (1.70 g, 4.49 mmol, 97% yield). 13CNMR (ppm, 500 MHz, CDCl3, 298 K) δ 161.588, 148.067, 145.802, 136.573, 135.924, 134.834, 129.444, 128.907, 128.029, 126.122, 123.236, 121.950, 118.038, 25.922. 1HNMR (ppm, 400 MHz, CDCl3, 298 K) δ: 8.049 (d, 1H, J=8.4 Hz), 7.976 (m, 1H), 7.958 (m, 1H), 7.758 (d, 1H, J=8.8 Hz), 7.701-7.657 (m, 1H), 7.599 (d, 1H, J=8.8 Hz), 7.554-7.507 (m, 2H), 7.346 (d, 1H, J=8.0 Hz), 2.785 (s, 3H). MS-ESI (m/z): [M+H]+ calculated for C16H13BrNO3S, 378.0 (79Br) and 380.0 (81Br); found 378.0 (79Br) and 379.9 (81Br).

Workup

  1. customSolvent was removed in vacuo, and residue
  2. dissolutionwas dissolved in EtOAc
  3. washwashed twice with saturated aq. NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. customSolvent was removed in vacuo
  6. customthe residue was purified by SiO2 column chromatography (Hexanes/EtOAc=1/1)

Sources & evidence

ORD record
ord-2a0210bf84464b6faec96dd13461172d
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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