Acetone → HCID 86603031, compound

HRID 735483Notes

Reaction equation

HRID 735483 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26](CC4OCCO4)[CH:25]=3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:36]([F:39])([F:38])[F:37])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.C[C:58](C)=[O:59]>>[CH2:1]([N:8]1[C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=3)[CH:58]=[O:59])=[CH:21][CH:22]=2)=[C:15]2[C:10]([C:11]([C:36]([F:37])([F:38])[F:39])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67021259HCID 67021259, compound

Product 1

HCID 86603031HCID 86603031, compound

Procedure

2-benzyl-3-[4-(3-[1,3]dioxolan-2-ylmethyl-phenoxy)-phenyl]-7-trifluoromethyl-2H-indazole (14 mg, 0.0264 mmol) was treated with 6.6 mg PPTS in 1.5 ml acetone under reflux for 2 hrs. The reaction mixture was extracted with NaHCO3 and CH2Cl2. The combined organic phases were dried, evaporated and the crude material was purified on a chromatotron using a gradient changing from 1:99 (EtOAc/heptane) to 3:7 (EtOAc/heptane) to afford 5 mg of analytically pure product.

Workup

  1. temperatureunder reflux for 2 hrs
  2. extractionThe reaction mixture was extracted with NaHCO3 and CH2Cl2
  3. customThe combined organic phases were dried
  4. customevaporated
  5. customthe crude material was purified on a chromatotron
  6. customto afford 5 mg of analytically pure product

Sources & evidence

ORD record
ord-e1d4b221f2fe42338faf018ac915b64c
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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