Triethylamine → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1410118

反応式

HRID 1410118 の反応式
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=2)[O:3]1.CC[N:21]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:21])=[O:14])=[CH:11][CH:10]=2)[O:3]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

生成物 1

HCID 27605884-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide収率 48.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45%) as a yellow solid. LC-MS: 248 [M+H]+, tR=1.421 min.

後処理

  1. customwas bubbled ammonia until saturation
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customto give residue which
  5. customwas purified by column chromatography (DCM:MeOH=50:1)

出典と根拠

ORDレコード
ord-55d2ce2fcf2240fba99cca6a54a2cb97
出典データセット
uspto-grants-2014_12
特許番号
US08921383B2

関連ノート

読み込み中…