Triethylamine → HCID 66876830, compound

HRID 2421241Notes

Reaction equation

HRID 2421241 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:13]([F:12])[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 247281734-Bromo-6-fluoro-1H-indole

Product 1

HCID 66876830HCID 66876830, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-6-fluoro-1H-indole (D16) (580 mg, 2.71 mmol) in dichloromethane (20 mL) was added {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (1.33 g, 5.42 mmol), copper (II) acetate (984 mg, 5.42 mmol), triethylamine (0.755 mL, 5.42 mmol) and powdered 4A molecular sieves (2 g, 2.71 mmol). The mixture was stirred at room temperature in the presence of air for 3 days. The reaction was filtered through a pad of celite and washed with dichloromethane. The organic solution was washed with water and then the aqueous phase re-extracted with dichloromethane. The combined organic phases were dried over magnesium sulphate, filtered and concentrated. The product was partially purified by silica gel chromatography eluting with 5-20% ethyl acetate in hexane to yield the title compound (D17), (980 mg).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washwashed with dichloromethane
  3. washThe organic solution was washed with water
  4. extractionthe aqueous phase re-extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was partially purified by silica gel chromatography
  9. washeluting with 5-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0a0629a0748b426f994497a19a17226a
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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