Hydrochloric Acid → 4-Cyclohept-1-enyl-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinoline-6-carbonitrile

HRID 2053457ノート

反応式

HRID 2053457 の反応式
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]([C:14]1[O:18][N:17]=[C:16]([CH3:19])[CH:15]=1)=[C:6]2OS(C(F)(F)F)(=O)=O)#[N:2].[C:28]1(B(O)O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:28]1([C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:9][C:8](=[O:13])[C:7]=2[C:14]2[O:18][N:17]=[C:16]([CH3:19])[CH:15]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 3434501Cyclohepten-1-ylboronic acidHCID 136355240Trifluoro-methanesulfonic acid 6-cyano-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester

生成物 1

HCID 1354400894-Cyclohept-1-enyl-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinoline-6-carbonitrile収率 58.3%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of trifluoro-methanesulfonic acid 6-cyano-3-(3-methyl-isoxazol-5-yl)-2-oxo-1,2-dihydro-quinolin-4-yl ester (30 mg, 0.075 mmol), cyclohepten-1-ylboronic acid (12.6 mg, 0.090 mmol), Pd(PPh3)4 (8.7 mg, 0.0075 mmol) and Na2CO3 (375 ul, 0.75 mmol, 2.0 M) in 1 ml of 1,4-dioxane was stirred at 80° C. for 1 h, then cooled to rt. Treated with 20 ml of H2O, the mixture was acidified to PH=7 with 1N HCl and then extracted with EtOAc (3×15 ml). The combined organic layers were washed with H2O (20 ml), brine (15 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10-20% EtOAc/DCM) gave 15.1 mg (58%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) δ 12.3 (s, 1H), 8.08 (d, 1H, J=1.7 Hz), 7.77 (dd, 1H, J=8.6, 1.7 Hz), 7.43 (d, 1H, J=8.6 Hz), 6.70 (s, 1H), 5.79 (t, 1H, J=6.1 Hz), 2.44 (s, 3H), 2.26-2.52 (m, 4H), 1.62-1.94 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C21H19N3O2, 346.2 (M+H), found 346.1.

後処理

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (3×15 ml)
  3. washThe combined organic layers were washed with H2O (20 ml), brine (15 ml)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-acd1af765af142a09609b1d8ad1214b2
出典データセット
uspto-grants-2008_02
特許番号
US07326788B2

反応ノート

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