Ammonia → HCID 86709675, compound

HRID 2285385Notes

Reaction equation

HRID 2285385 reaction equation
[NH3:1].C(O)C.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH:25]=O)=[C:10]([NH:12][C:13](=O)[CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:15])[CH:11]=1>>[Br:5][C:6]1[CH:11]=[C:10]2[C:9]([CH:25]=[N:1][C:13]([CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:15])=[N:12]2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 702Ethanol2×HCID 86709676HCID 86709676, compound2×

Product 1

HCID 86709675HCID 86709675, compoundYield 94%

Conditions

Temperature
150 °C

Procedure

A solution of ammonia in ethanol (2 M, 14 mL, 28 mmol) was added to N-(5-bromo-2-formyl-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-propionamide (0.5 g, 1.36 mmol). The mixture was heated in a microwave reactor at 150° C. for 2 h. A second solution of ammonia in ethanol (2 M, 14 mL, 28 mmol) was added to N-(5-bromo-2-formyl-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-propionamide (1.0 g, 2.72 mmol). The mixture was heated in a microwave reactor at 150° C. for 2 h. The two resultant solutions were combined and evaporated and the residue purified by silica gel chromatography using iso-hexanes/dichloromethane 1:1 to 1:3 to 0:1 to yield the title compound (1.34 g, 94%) as a yellow gum. 1H NMR (300 MHz, CDCl3) δ 0.08 (s, 6H), 0.91 (s, 9H), 1.64 (d, J=6.7 Hz, 3H), 5.22 (q, J=6.5 Hz, 1H), 7.71-7.83 (m, 2H), 8.26 (s, 1H), 9.40 (s, 1H). LCMS (m/z) 367.0, 369.0 [M+H], Tr=4.00 min.

Workup

  1. temperatureThe mixture was heated in a microwave reactor at 150° C. for 2 h
  2. customevaporated
  3. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-2c1cf2d42f464b7fb87f70a77e4ab469
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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