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

HRID 1410118

반응식

HRID 1410118 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-55d2ce2fcf2240fba99cca6a54a2cb97
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

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