Boron tribromide → HCID 67004288, compound

HRID 1513891Notes

Reaction equation

HRID 1513891 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=1)=[O:14])=[C:8]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[C:31]=1[F:38])[CH:7]=[CH:6]2.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl.C(O)(C)C>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[CH:19][CH:20]=1)=[O:14])=[C:8]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[C:31]=1[F:38])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21906603Chloroform isopropyl alcoholHCID 57552528HCID 57552528, compound

Product 1

HCID 67004288HCID 67004288, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [6-methoxy-2-(2,3,4-trifluoro-phenyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (880 mg, 1.69 mmol) in 100 mL methylene chloride and chill in ice. Add 4.0 mL of neat boron tribromide with swirling and stir in the ice bath for 30 minutes. Allow the mixture to come to room temp and stir for an additional 1 hour. Carefully pour the mixture into a two-phase system consisting of saturated sodium bicarbonate solution and a 3/1 mixture of chloroform/isopropanol. Separate the organic layer, dry over 3 Å molecular sieves and evaporate to give 800 mg of slightly impure product. Purify on a silica gel column eluting with 3% methanol/methylene chloride to give 635 mg (74%) of the title compound: 1H-NMR (CD3OD, 400 MHz) δ7.89 (d, J=8.8 Hz, 1H); 7.69-7.42 (m, 4H); 7.45-7.42 (m, 1H); 7.31 (d, J=2.4 Hz, 1H); 7.14 (dd, J=9.2, 2.4 Hz, 1H); 7.02-6.87 (m, 3H); 4.20 (t, J=5.6 Hz, 2H); 2.84 (t, J=5.6 Hz, 2H); 2.59-2.59 (m, 4H); 1.71-1.65 (m, 4H); 1.56-1.53 (m, 2H).

Workup

  1. temperaturechill in ice
  2. customto come to room temp
  3. additionCarefully pour the mixture into a two-phase system
  4. customSeparate the organic layer
  5. customdry over 3 Å molecular sieves
  6. customevaporate
  7. customto give 800 mg of slightly impure product
  8. customPurify on a silica gel column
  9. washeluting with 3% methanol/methylene chloride

Sources & evidence

ORD record
ord-a5523ff7ebd34164ae50131eafe7a054
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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