Boron tribromide → HCID 67004256, compound

HRID 1513884Notes

Reaction equation

HRID 1513884 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].B(Br)(Br)Br.C(Cl)(Cl)Cl.C(O)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21906603Chloroform isopropyl alcoholHCID 57552529HCID 57552529, compound

Product 1

HCID 67004256HCID 67004256, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [2-(2,6-difluorophenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)-phenyl]-methanone (1.5 gm., 3.0 mmoles) in 500 ml methylene chloride and chill in ice. To this solution add boron tribromide (6.0 ml, 63 mmoles) in portions with swirling between additions. Allow to come to room temp. and stir for one hour. Pour into a two-phase system consisting of an organic layer of 3/1 chloroform/isopropanol and an aqueous layer of saturated sodium bicarbonate. Separate the phases and dry the organic layer using 3A molecular sieves. Purify on a silica column eluting with a 0-10% methanol/methylene chloride gradient. The yield of pure product is 600 mg (44%): 1H-NMR (CD3OD, 400 MHz) δ7.87 (d, J=8.0 Hz, 1H); 7.56 (d, J=8.4 Hz, 2H); 7.49 (d, J=9.2 Hz, 1H); 7.33 (d, j=8.8 Hz, 1H); 7.27-7.25 (m, 1H); 7.23-7.21 (m, 1H); 7.06 (dd, J=8.8, 2.4 Hz, 1H); 6.86-6.79 (m, 4H); 4.14 (t, J=5.6 Hz, 2H); 2.76 (t, J=5.6 Hz, 2H); 2.53-2.53 (m, 4H); 1.65-1.59 (m, 4H); 1.50-1.46 (m, 2H).

Workup

  1. temperaturechill in ice
  2. customto come to room temp.
  3. additionPour into a two-phase system
  4. customSeparate the phases
  5. customdry the organic layer
  6. customPurify on a silica column
  7. washeluting with a 0-10% methanol/methylene chloride gradient

Sources & evidence

ORD record
ord-25c6b7ef3dca45179fe91daef74bb967
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

Loading…