Boron tribromide → HCID 25008128, compound

HRID 2093183Notes

Reaction equation

HRID 2093183 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[C:35]([O:36]C)=[CH:34][CH:33]=[C:32]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[CH3:44])[CH:31]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.B(Br)(Br)Br>ClCCl>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[C:35]([OH:36])=[CH:34][CH:33]=[C:32]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[CH3:44])[CH:31]=3)[C@H:14]2[CH3:45])[CH:4]=[C:3]([C:2]([F:1])([F:47])[F:46])[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86630540HCID 86630540, compound

Product 1

HCID 25008128HCID 25008128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold solution (−78° C. bath) of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[6′-methoxy-2″-methyl-4-(trifluoromethyl)-1,1′:3′,1″-terphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (75 mg, 0.11 mmol) in dichloromethane (1 mL) was added boron tribromide (106.6 mg, 0.426 mmol). The resulting mixture was aged cold (−78° C. bath) for 1 hour then allowed to warm to ambient temperature overnight. Reaction was quenched with ice followed by extraction with dichloromethane. The combined extracts were washed with brine and then over Na2SO4. The resulting mixture was filtered and concentrated. The residue was purified by preparative TLC on SiO2 (eluted with 30% ethyl acetate in hexanes) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[6′-hydroxy-2″-methyl-4-(trifluoromethyl)-1,1′:3′,1″-terphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=653.16; found=654.19 (M+1)+. 1H NMR signals are doubled because of atropoisomerism 1H NMR (CDCl3, 500 MHz) δ 7.87-7.84 (m, 1H), 7.76 (s, 0.5H), 7.72-7.65 (m, 2.5H), 7.63 (s, 1H), 7.53-7.47 (m, 1H), 7.33-7.23 (m, 3H), 7.23-7.16 (m, 2H), 7.12 (dd, J=10.5, 2.5 Hz, 1H), 7.04 (d, J=8.0 Hz, 0.5H), 7.02 (d, J=8.5 Hz, 0.5H), 5.64 (d, J=8.0 Hz, 0.5H), 5.32 (d, J=7.5 Hz, 0.5H), 4.98, 4.92 (d, J=16 Hz, 1H), 4.23 (d, J=15.5 Hz, 0.5H), 4.07 (d, J=15.5 Hz, 0.5H), 3.89-3.82 (m, 0.5H), 3.74-3.67 (m, 0.5H), 2.32, 2.28 (s, 3H), 0.58 (d, J=7 Hz, 1.5H), 0.49 (d, J=6.5 Hz, 1.5H).

Workup

  1. customcold (−78° C. bath)
  2. customfor 1 hour
  3. customReaction
  4. customwas quenched with ice
  5. extractionfollowed by extraction with dichloromethane
  6. washThe combined extracts were washed with brine
  7. filtrationThe resulting mixture was filtered
  8. concentrationconcentrated
  9. customThe residue was purified by preparative TLC on SiO2 (eluted with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6ebf0c55b18a4288a461c36a4a7234df
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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