Boron Trichloride → HCID 10074312, compound

HRID 915510Notes

Reaction equation

HRID 915510 reaction equation
B(Cl)(Cl)Cl.[CH3:5][NH:6][C:7]([C:9]1[C:13]2[CH:14]=[C:15]([O:24][CH:25]([CH3:27])C)[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:17][C:12]=2[O:11][C:10]=1[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:8]>ClCCl>[CH3:5][NH:6][C:7]([C:9]1[C:13]2[CH:14]=[C:15]([O:24][CH2:25][C:27]3[CH:29]=[CH:28][C:10]([O:11][CH3:12])=[CH:9][CH:7]=3)[C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:17][C:12]=2[O:11][C:10]=1[C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)=[O:8]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 10047296HCID 10047296, compound

Product 1

HCID 10074312HCID 10074312, compoundYield 127.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation of compound 30 (a) (2-(4-fluoro-phenyl)-5-hydroxy-6-morpholin-4-yl-benzofuran-3-carboxylic acid methylamide). Boron trichloride (1M solution in xylenes, 5.0 mL, 5.0 mmol) was added to a solution of 2-(4-fluoro-phenyl)-5-isopropoxy-6-morpholin-4-yl-benzofuran-3-carboxylic acid methylamide (0.71 g, 1.7 mmol, which can be prepared according to Example 24, above), dissolved in dichloromethane (30 mL). The reaction mixture was refluxed for 30 minutes, cooled to room temperature, quenched with 1M hydrochloric acid (10 mL) and stirred for 1 hour. The organics were removed by evaporation, and a saturated solution of sodium bicarbonate was added until pH=8-9. The product was extracted with ethyl acetate and purified via column chromatography (dry loading onto silica gel, ethyl acetate/hexanes gradient) to provide 0.53 g (84%) of the desired product.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. customquenched with 1M hydrochloric acid (10 mL)
  3. customThe organics were removed by evaporation
  4. additiona saturated solution of sodium bicarbonate was added until pH=8-9
  5. extractionThe product was extracted with ethyl acetate
  6. custompurified via column chromatography (dry loading onto silica gel, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-3a374bdd79794c25ad171366db8bbd81
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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