N-Iodosuccinimide → 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-iodomethyl-6,7-dihydro-8-oxa-1,4,8b-triaza-as-indacene

HRID 348037Notes

Reaction equation

HRID 348037 reaction equation
[CH2:1]([C:4]1[CH:5]=[N:6][C:7]2[N:8]([N:11]=[C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]=1[OH:10])[CH:2]=[CH2:3].[I:28]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:12]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:7]2[N:8]([C:9]3[O:10][CH:2]([CH2:3][I:28])[CH2:1][C:4]=3[CH:5]=[N:6]2)[N:11]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178439549HCID 178439549, compound

Product 1

HCID 100069482-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-iodomethyl-6,7-dihydro-8-oxa-1,4,8b-triaza-as-indacene

Reagents, catalysts & solvents 1

HCID 18399249Chloroform dichloromethaneSolvent

Procedure

To a mixture of 6-allyl-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidin-7-ol (I-15A-1a; 25 mg, 0.063 mmol) in 9:1 methylene chloride/chloroform (0.63 ml) at 0° C. was added N-iodosuccinimide (15 mg, 0.066 mmol), portionwise. The reaction was stirred overnight at room temperature and then extracted from water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo. Purification on a Biotage™ Flash 12S column using 20% ethyl acetate in hexanes as eluant afforded compound 15A-1 (15 mg, 46%) as a solid: +ESI MS (M+1) 522.3; 1H NMR (400 MHz, CD3OD) δ 8.46 (s, 1H), 7.53–7.40 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.45–5.41 (m, 1H), 3.81–3.64 (m, 2H), 3.33 (d, J=6.2 Hz, 2H).

Workup

  1. extractionextracted from water with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated, in vacuo
  5. customPurification on a Biotage™ Flash 12S column
  6. customafforded compound 15A-1 (15 mg, 46%) as a solid

Sources & evidence

ORD record
ord-45c210288c4843b49c840a060e68abf2
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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