Water → HCID 23121807, compound

HRID 552604Notes

Reaction equation

HRID 552604 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:29])[C:12]2[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])[CH:13]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br.O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:29])[C:12]2[CH:13]=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])[CH:15]=[C:16]([O:18][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[Cl:30])[CH:17]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11905alpha-Bromo-o-chlorotolueneHCID 23121806HCID 23121806, compound

Product 1

HCID 23121807HCID 23121807, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of N-(5-nitropyridin-2-yl)-3-[(2-cyanobenzyl)oxy]-5-hydroxybenzamide (195 mg) in DMF (3 ml) was treated with Ag2CO3 (165 mg) and 2-Chlorobenzyl bromide (0.073 ml). Heated to 85° C. and stirred for 17 hours under Nitrogen. Allowed to cool to ambient temperature. Water (25 ml) added. Extracted with ethyl acetate (50 ml), washed with brine (25 ml), dried over MgSO4. Volatile material was removed by evaporation to give a solid, which was purified by flash chromatography on silica eluted with 0-5% ethyl acetate in dichloromethane to give the title compound (43 mg) as a solid, 1H NMR δ (d6-DMSO): 5.20 (s, 2H), 5.33 (s, 2H), 6.96 (s, 1H), 7.40 (m, 5H), 7.57 (m, 2H), 7.72 (m, 2H), 7.90 (d, 1H), 8.40 (d, 1H), 8.64 (dd, 1H), 9.22 (s, 1H), 11.50 (s, 1H). LCMS rt=3.27 min (97.4%), ES+ 515.50 (M+H)+.

Workup

  1. temperatureAllowed to cool to ambient temperature
  2. extractionExtracted with ethyl acetate (50 ml)
  3. washwashed with brine (25 ml)
  4. dry with materialdried over MgSO4
  5. customVolatile material was removed by evaporation
  6. customto give a solid, which
  7. customwas purified by flash chromatography on silica
  8. washeluted with 0-5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-079fa19f1dc74d81ab981ffc5ff0b0cb
Source dataset
uspto-grants-2011_05
Patent number
US07951830B2

Reaction notes

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