Diisopropylethylamine → 2-(dimethylamino)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

HRID 502650Notes

Reaction equation

HRID 502650 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.C(N(C(C)C)CC)(C)C.[CH3:26][N:27]([CH3:32])[CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH3:26][N:27]([CH3:32])[CH2:28][C:29]([NH:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 70103442-(Dimethylamino)acetyl chloride

Product 1

HCID 594278312-(dimethylamino)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round bottom flask was placed 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 65 (438 mg, 2 mmol), dichloromethane (30 mL), diisopropylethylamine (517 mg, 4 mmol), and 2-(dimethylamino)acetyl chloride (267 mg, 2.2 mmol). The reaction was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure. Saturated aqueous sodium bicarbonate was added (20 mL), and the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude was purified on a silica-gel column using 0 to 20% methanol in dichloromethane as the solvent gradient. The product fractions were collected and concentrated to afford the title compound 66 as an orange oil. Mass found by LC-MS(+): 305 (M+H); calc. for C16H25BN2O3: 304.19.

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. customThe solvent was removed under reduced pressure
  3. additionSaturated aqueous sodium bicarbonate was added (20 mL)
  4. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified on a silica-gel column
  9. customThe product fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0d2c098d90404eca9e2fafc76d8573e1
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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