Tetrahydrofuran → HCID 10142972, compound

HRID 2373473Notes

Reaction equation

HRID 2373473 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]([O:10][CH2:11][C:12]1[N:13]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)=[CH:16][CH:15]=2)(=[O:9])[CH3:8].C1C[O:43]CC1>>[C:7]([O:10][CH2:11][C:12]1[N:13]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[C:14]2[C:19]([C:20]=1[C:1](=[O:5])[C:2]([OH:43])=[O:3])=[CH:18][C:17]([C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:25][CH:26]=1)=[CH:16][CH:15]=2)(=[O:9])[CH3:8]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 21964303HCID 21964303, compound

Product 1

HCID 10142972HCID 10142972, compound

Procedure

Oxalyl chloride (1.05 mL) was added dropwise to a stirring solution of {1-(4-methylbenzyl) -5-[4-(trifluoromethoxy)phenyl]-1H-indol-2-yl}methyl acetate (0.515 g) in THF (17 mL) at room temperature over a period of 5 minutes under a nitrogen atmosphere. After the reaction mixture was stirred at room temperature for 4 hours, the reaction was quenched carefully with water. The aqueous mixture was extracted with ethyl acetate. The extract was washed with water, and brine, dried over anhydrous magnesium sulfate, and concentrated to give the title compound as a light brown solid, mp: 79-80° C. Mass spectrum (ESI, [M−H]−) m/z 524. 1HNMR (400 MHz, DMSO-d6): δ 14.50 (br s, 1H), 8.20 (s, 1H), 7.74 (d, 2H, J=8.55 Hz), 7.70 (d, 1H, J=8.69 Hz), 7.62 (d, 1H, J=8.55 Hz), 7.47 (d, 2H, J=8.25 Hz), 7.15 (d, 2H, J =7.88 Hz), 6.99 (d, 2H, J=7.78 Hz), 5.64 (s, 2H), 5.53 (s, 2H), 2.25 (s, 3H), and 1.83 ppm (s, 3H).

Workup

  1. customthe reaction was quenched carefully with water
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. washThe extract was washed with water, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf5267b8c9c4c39b59e9316bcac1df1
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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