Iodine → HCID 89754670、化合物

HRID 575431

反応式

HRID 575431 の反応式
[F:1][C:2]1[C:14]([Sn](C)(C)C)=[CH:13][C:5]2[CH2:6][C:7](=[O:12])[CH:8]3[CH2:11][CH:10]([C:4]=2[CH:3]=1)[CH2:9]3.[I:19]I.BrC1C(F)=CC2C3CC(C(=O)CC=2C=1)C3.[SnH4]>C(Cl)(Cl)Cl>[F:1][C:2]1[C:14]([I:19])=[CH:13][C:5]2[CH2:6][C:7](=[O:12])[CH:8]3[CH2:11][CH:10]([C:4]=2[CH:3]=1)[CH2:9]3

参加物

6

反応物 4

HCID 807Iodine2 回HCID 123161StannaneHCID 86693513HCID 86693513、化合物HCID 89754796HCID 89754796、化合物

生成物 1

HCID 89754670HCID 89754670、化合物収率 45%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a rapidly stirred solution of crude of 3-fluoro-2-(trimethylstannyl)-6,7-dihydro-5H-5,7-methanobenzo[7]annulen-8(9H)-one (3.09 g at 37% purity LCMS-UV215) in chloroform (20 mL) at room temperature was introduced dropwise a solution of iodine (1.488 g, 5.86 mmol, 1.0 equivalent with respect to number of moles 5-bromo-4-fluorotricyclo[8.1.1.02,7]dodeca-2(7),3,5-trien-9-one used for stannane synthesis in previous synthetic step, as a saturated solution in chloroform). Following addition of the iodine solution, the reaction mixture was evaporated directly onto silica gel in vacuo. The dry-loaded material was purified by silica gel flash column chromatography (eluent: heptane/ethyl acetate gradient) to furnish the title compound (0.835 g, 2.64 mmol, 45% over 2 steps) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 2.08-2.14 (m, 2H), 2.87-2.96 (m, 2H), 3.22-3.28 (m, 1H), 3.48 (td, J=8.28, 3.63 Hz, 1H), 4.11 (s, 2H), 6.78 (d, J=8.51 Hz, 1H), 7.53 (d, J=6.31 Hz, 1H); M+H=317

後処理

  1. customthe reaction mixture was evaporated directly onto silica gel in vacuo
  2. customThe dry-loaded material was purified by silica gel flash column chromatography (eluent: heptane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-69a12fef8e944fc3bb07bc8d1e539d28
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

関連ノート

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