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

HRID 1410118

Reaction equation

HRID 1410118 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-55d2ce2fcf2240fba99cca6a54a2cb97
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Linked notes

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