Cesium carbonate → methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]benzoate

HRID 29681Notes

Reaction equation

HRID 29681 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1.[C:33]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:37][C:36]([CH:39]=[N:40][OH:41])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:41]/[N:40]=[CH:39]/[C:36]2[CH:37]=[CH:38][C:33]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[CH:34][CH:35]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2615464-PhenylbenzaldoximeHCID 865974012-(3,5-Bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

Product 1

HCID 87734636methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]benzoateYield 68.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was produced using similar methods as those used in Step 5, example 27, starting with 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.35 g, 0.66 mmol), biphenyl-4-carbaldehyde oxime (0.14 g, 0.70 mmol) and cesium carbonate (0.86 g, 2.65 mmol) in acetone (25 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[3,5-bis(trifluoromethyl)benzoyl]amino}benzoic acid methyl ester (0.29 g, 68%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.79 (s, 1H), 8.52 (s, 2H), 8.43 (s, 1H), 8.31 (s, 1H), 8.11 (d, 1H), 7.98 (d, 1H), 7.97-7.64 (AA′BB′, 4H), 7.45 (t, 2H), 7.37 (t, 1H), 6.89 (dd, 1H), 4.31 (t, 2H), 4.23 (t, 2H), 3.84 (s, 3H), 2.18 (m, 2H).

Workup

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-826b4e4f086549189de27a24b99979a2
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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