p-Toluenesulfonic acid → HCID 71295526, compound

HRID 1776874Notes

Reaction equation

HRID 1776874 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21](O)=[C:20]([C:25]2[NH:26][C:27]3[C:32]([C:33]=2[Cl:34])=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:19]=1>C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]2[O:5][CH:4]([CH:1]3[CH2:3][CH2:2]3)[N:26]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[C:33]([Cl:34])=[C:25]3[C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 123114CyclopropanecarboxaldehydeHCID 71295631HCID 71295631, compound

Product 1

HCID 71295526HCID 71295526, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Cyclopropanecarbaldehyde (70 mg, 1.0 mmol) and PTSA (17 mg, 0.1 mmol) were added to a solution of 4-bromo-2-(3-chloro-1H-indol-2-yl)phenol (110 mg, 0.34 mmol) in toluene (2 mL). The mixture was allowed to stir at 110° C. for about 15 hours. The reaction solution was extracted by EtOAc, and the combined organic layers were washed with H2O (3×10 mL), brine and dried over Na2SO4. The solvent was removed and the crude product was Purified using prep-TLC to provide the desired product of 2-bromo-12-chloro-6-cyclopropyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole (40 mg, yield: 31.3%). 1H-NMR (CDCl3, 400 MHz) δ 8.42 (m, 1H), 7.63 (t, J=0.4 Hz, 1H), 7.30˜7.35 (m, 2H), 7.15˜7.24 (m, 2H), 6.93 (m, 1H), 5.62 (d, J=0.8 Hz, 1H), 1.36˜1.45 (m, 1H), 0.50˜0.56 (m, 4H). MS (M+H)+: 374/376.

Workup

  1. extractionThe reaction solution was extracted by EtOAc
  2. washthe combined organic layers were washed with H2O (3×10 mL), brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customthe crude product was Purified

Sources & evidence

ORD record
ord-7f017da1f40f4ce0b8f490452d27803a
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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