Tin tetrachloride → HCID 11998204, compound

HRID 1259810Notes

Reaction equation

HRID 1259810 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:25][C:26](O)=[O:27])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]3=[O:24])=[CH:9][C:4]=2[O:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl>CN(C=O)C.C1(C)C=CC=CC=1.ClCCl>[CH2:19]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2([C:8]3[C:7](=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[C:26](=[O:27])[CH2:25]2)[C:11]1=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 3

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 545864982-(3-(Benzo[d][1,3]dioxol-5-yl)-2-oxo-1-pentylindolin-3-yl)acetic acid

Product 1

HCID 11998204HCID 11998204, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(1,3-benzodioxol-5-yl)-2-oxo-1-pentyl-2,3-dihydro-1H-indol-3-yl]acetic acid (0.28 g, 0.73 mmol) was added one drop of DMF and oxalyl chloride (0.32 mL, 3.7 mmol) in toluene (10 mL). The mixture was stirred at ambient temperature overnight and concentrated under vacuum to dryness to afford a brown oil. This substance was dissovled in dichloromethane (15.0 mL) followed by the addition of tin (IV) chloride (0.07 mL, 0.57 mmol) at 0° C. The mixture was stirred at ambient temperature overnight and quenched with ice water. The mixture was poured into water (100 mL), and the mixture was extracted with dichloromethane (150 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.09 g, 67%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.31 (td, 1H), 7.14 (s, 1H), 7.02 (td, 1H), 6.97-6.92 (m, 2H), 6.22 (s, 1H), 6.03-5.98 (m, 2H), 3.87-3.63 (m, 2H), 3.17 (d, 1H), 2.85 (d, 1H), 1.79-1.66 (m, 2H), 1.41-1.30 (m, 4H), 0.88 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 201.4, 177.5, 154.8, 151.8, 149.6, 143.1, 132.5, 131.6, 128.9, 123.4, 123.2, 108.9, 103.5, 102.6, 102.5, 53.8, 47.7, 40.5, 29.0, 27.1, 22.3, 14.0; MS (ES+), m/z 386.1 (M+23), 364.1 (M+1).

Workup

  1. concentrationconcentrated under vacuum to dryness
  2. customto afford a brown oil
  3. stirringThe mixture was stirred at ambient temperature overnight
  4. customquenched with ice water
  5. additionThe mixture was poured into water (100 mL)
  6. extractionthe mixture was extracted with dichloromethane (150 mL)
  7. washThe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-940f256416c745bf8210e09828b41d50
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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