Diisopropylethylamine → 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide

HRID 1777522Notes

Reaction equation

HRID 1777522 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6][NH2:7].[F:10][C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:10][C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH:7][CH2:6][CH2:5][C:4]#[C:3][Si:2]([CH3:9])([CH3:8])[CH3:1])=[O:19]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19703099(4-Aminobut-1-yn-1-yl)trimethylsilaneHCID 67974126HCID 67974126, compound

Product 1

HCID 679746653-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamideYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(trimethylsilyl)but-3-yn-1-amine (0.184; 1.30 mmol), 3-(3-fluorobenzyl)benzoic acid, (0.200 g; 0.869 mmol), HATU (0.363 g; 0.955 mmol) and N,N-diisopropylethylamine (0.374 mL; 2.17 mmol) in DMF (20 mL) was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was washed with water, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) to afford 0.13 g (42%) of 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide which was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2fbd499dd21c46d4bac2b057a5cdf548
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…