1-benzyl-1H-indole-2-carbaldehyde → 4-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-3-[4-(trifluoromethyl)phenyl]benzoic acid

HRID 1392288Notes

Reaction equation

HRID 1392288 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][NH2:16])=[CH:9][CH:10]=1)=[O:4].[CH2:27]([N:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35]1[CH:43]=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([N:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[C:35]1/[CH:43]=[N:16]/[O:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[C:7]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=2)=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][CH:9]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 129167171-benzyl-1H-indole-2-carbaldehydeHCID 691944346-(3-Aminooxy-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 115198114-[3-[(E)-(1-benzylindol-2-yl)methylideneamino]oxypropoxy]-3-[4-(trifluoromethyl)phenyl]benzoic acidYield 54%

Procedure

This compound was produced using similar methods as those used in Step 6, example 4, starting with 6-(3-aminooxy-propoxy)-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.25 g, 0.68 mmol) and 1-benzyl-1H-indole-2-carbaldehyde (0.16 g, 0.68 mmol). The crude material was purified by recrystallizing two times from ethyl acetate/hexanes followed by HPLC (82% acetonitrile in 0.1% trifluoroacetic acid solution) and one final recrystallization from ethyl acetate/hexanes to give 6-[3-({[(1E)-(1-benzyl-1H-indol-2-yl)methylidene]amino}oxy)propoxy]-4′-(trifluoromethyl)-1,1 ′-biphenyl-3-carboxylic acid (0.21 g, 54%) as a white solid. mp=196-197° C. 1H NMR (400 MHz, DMSO-d6); δ 12.80 (bs, 1H), (s, 1H), 7.96 (dd, 1H), 7.88 (d, 1H), 7.74 (AA′BB′, 4H), 7.60 (d, 1H), 7.46 (d, 1H), 7.22-7.16 (m, 4H), 7.12 (t, 1H), 7.06 (t, 1H), 6.94 (d, 2H), 6.89 (s, 1H), 5.72 (s, 2H), 4.13 (t, 2H), 4.11 (t, 2H), 2.49 (m, 2H). Mass spec; (ES−) m/z 571.2. Elemental analysis; Calculated for C33H27F3N2O4: C, 69.22; H, 4.75; N, 4.89. Found: C, 69.04; H, 4.55; N, 4.82.

Workup

  1. customThis compound was produced
  2. customThe crude material was purified
  3. customby recrystallizing two times from ethyl acetate/hexanes
  4. customrecrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-53fcdd03b43146f8b350073ae11c8ac9
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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