Benzaldehyde → HCID 68239405, compound

HRID 1776836Notes

Reaction equation

HRID 1776836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([C:34]5[NH:35][C:36]6[C:41]([CH:42]=5)=[CH:40][CH:39]=[CH:38][CH:37]=6)[CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[CH3:43][C:44]1[CH:45]=[CH:46][C:47](S(O)(=O)=O)=[CH:48][CH:49]=1.C(=O)C1C=CC=CC=1.O>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:23])=[O:24])[C:18]([C:27]4[CH:28]=[C:29]5[C:34]6[NH:35][C:36]7[C:41]([C:42]=6[CH:43]([C:44]6[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=6)[O:33][C:30]5=[CH:31][CH:32]=4)=[CH:40][CH:39]=[CH:38][CH:37]=7)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 68239709HCID 68239709, compound

Product 1

HCID 68239405HCID 68239405, compoundYield 175.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(4-fluorophenyl)-5-(4-hydroxy-3-(1H-indol-2-yl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 g, 0.08 mmol), PTSA (3.0 mg, 0.017 mmol), and benzaldehyde (42 mg, 0.41 mmol) in xylene (2 mL) was stirred at 130° C. for 2 h under microwave. Water was added, extracted with EtOAc, the organic layer was washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using prep-TLC to provide the product of compound 63 (20 mg, yield: 38%). 1H-NMR (CDCl3, 400 MHz) δ 8.96 (s, 1H), 7.88˜7.92 (m, 2H), 7.76 (s, 1H), 7.65 (s, 1H), 7.50 (s, 1H), 7.32˜7.47 (m, 6H), 7.14˜7.17 (m, 4H), 6.96˜6.99 (m, 2H), 6.86 (s, 1H), 6.55 (s, 1H), 5.91 (d, J=4.8 Hz, 1H), 3.02 (s, 3H), 2.98 (d, J=4.8 Hz, 3H), 2.94 (s, 3H). MS (M+H)+: 672.

Workup

  1. extractionextracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-cbfcfb33e6b3465393caa4017d4c1577
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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