Dichloromethane → HCID 10319141, compound

HRID 915509Notes

Reaction equation

HRID 915509 reaction equation
B(Cl)(Cl)Cl.[CH3:5][NH:6][C:7]([C:9]1[C:13]2[CH:14]=[C:15]([O:23][CH:24](C)C)[C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][C:12]=2[O:11][C:10]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:8].Cl[CH2:35]Cl>>[CH3:5][NH:6][C:7]([C:9]1[C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[CH3:35])=[CH:17][C:12]=2[O:11][C:10]=1[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)=[O:8]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 10409873HCID 10409873, compound

Product 1

HCID 10319141HCID 10319141, compoundYield 100%

Procedure

Preparation of compound 29(a) (2-(4-fluoro-phenyl)-5-hydroxy-6-methanesulfonylamino-benzofuran-3-carboxylic acid methylamide). Boron trichloride (60 mL of 1M dichloromethane) was added for 10 minutes to 2-(4-fluoro-phenyl)-5-isopropoxy-6-methanesulfonylamino-benzofuran-3-carboxylic acid methylamide (7.10 g, 16.9 mmol, which can be prepared according to one of the procedures described in Example 21), in dichloromethane (200 mL). The mixture was stirred for 20 hours, and then carefully quenched with 1N HCl (10 mL). An additional amount of 4N HCl (100 mL) was added, and the reaction mixture was stirred for 24 hours. The precipitated solid was filtered off, washed with water, dried, and triturated with ethyl acetate/hexanes to provide 6.39 g (100%) of the desired product as a white solid.

Workup

  1. customcan be prepared
  2. customcarefully quenched with 1N HCl (10 mL)
  3. additionAn additional amount of 4N HCl (100 mL) was added
  4. stirringthe reaction mixture was stirred for 24 hours
  5. filtrationThe precipitated solid was filtered off
  6. washwashed with water
  7. customdried
  8. customtriturated with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d5d52f716c8746b9b82494c7a65169b8
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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