Iodine → (e)-(5-Iodo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-dimethylaminophenyl)-ethylene

HRID 1890161ノート

反応式

HRID 1890161 の反応式
[I:1]I.C([Sn](CCCC)(CCCC)[C:8]1[CH:9]=[C:10](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:11]=[N:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][F:23])CCC.C(Cl)Cl>C1COCC1>[I:1][C:8]1[CH:9]=[C:10](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][C:29]([N:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH:11]=[N:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][F:23]

参加物

5

反応物 3

HCID 807IodineHCID 6344DichloromethaneHCID 16221623(E)-(5-tri-Butylstannyl-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-dimethylaminophenyl)-ethylene

生成物 1

HCID 16221507(e)-(5-Iodo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-dimethylaminophenyl)-ethylene収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of iodine (I2, 0.063 g, 0.24 mmol) in THF (2 mL) was added dropwise to an ice bath cooled solution of 12a (0.114 g, 0.172 mmol) in THF (3 mL). After the addition, the reaction was stirred at 0° C. for 1 h. Following standard workup with CH2Cl2, the crude product was purified by FC (EtOAc/Hexanes, 25/75) to give a light yellow solid 13a (0.037 g, 48%). 1H NMR δ8.22 (d, 1H, J=2.1 Hz), 8.10 (d, 1H, J=2.1 Hz), 7.38 (d, 2H, J=8.8 Hz), 6.92 (d, 1H, J=16.3 Hz), 6.72 (d, 1H, J=16.3 Hz), 6.71 (d, 2H, J=8.8 Hz), 4.72-4.67 (m, 1H), 4.54-4.44 (m, 3H), 3.93-3.69 (m, 8H), 3.00 (s, 6H). 13C NMR δ 160.4, 150.5, 144.6, 144.55, 129.8, 129.5, 127.8, 125.3, 118.8, 112.6, 85.1, 81.7, 80.6, 71.3, 71.1, 70.8, 70.5, 69.6, 67.1, 40.6. HRMS calcd for C21H26FIN2O3 (M+), 500.0972. found, 500.0959.

後処理

  1. additionAfter the addition
  2. customthe crude product was purified by FC (EtOAc/Hexanes, 25/75)

出典と根拠

ORDレコード
ord-927085ad9e444a78be4d6cd08191c469
出典データセット
uspto-grants-2013_08
特許番号
US08506929B2

反応ノート

読み込み中…