Trimethyl borate → 8,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

HRID 2277349ノート

反応式

HRID 2277349 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]2([CH3:23])[CH3:22])[CH:15]=1.C([Li])CCC.[B:29](OC)([O:32]C)[O:30]C>C1COCC1.C1CCCCC1>[CH3:22][C:5]1([CH3:23])[C:4]2[C:13]3=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[N:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=3)[CH:15]=[C:2]([B:29]([OH:32])[OH:30])[CH:3]=2

参加物

6

反応物 3

HCID 8470Trimethyl borateHCID 671097356-Bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridineHCID 178418339Butyllithium

生成物 1

HCID 673261988,8-Dimethyl-8H-indolo[3,2,1-de]acridine-6-boronic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒

実験手順

93.7 g (259 mmol) of 6-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine are dissolved in 1500 ml of dry THF, 135 ml (337 mmol) of a 2.5 M solution of n-butyllithium in cyclohexane are added dropwise at −70° C., after 1 h 37 ml of trimethyl borate (336 mmol) are added dropwise, the mixture is warmed to room temperature over the course of 1 h, the solvent is removed, and the residue, which is uniform according to 1H-NMR, is employed in the subsequent reaction without further purification.

後処理

  1. additionare added dropwise
  2. customthe solvent is removed
  3. customis employed in the subsequent reaction without further purification

出典と根拠

ORDレコード
ord-b811b8c28ad6423b8fe72bc2ee85c13d
出典データセット
uspto-grants-2015_09
特許番号
US09133119B2

反応ノート

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