Boron tribromide → HCID 59485723, compound

HRID 1972281Notes

Reaction equation

HRID 1972281 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[C@H:11]([CH2:21][N:22]3[N:26]=[N:25][C:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[N:23]3)[O:10][C:9]2=[O:33])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[C@H:11]([CH2:21][N:22]3[N:26]=[N:25][C:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[N:23]3)[O:10][C:9]2=[O:33])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59485840HCID 59485840, compound

Product 1

HCID 59485723HCID 59485723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a 10 mL round bottom flask is charged with (4S,5S)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-5-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)oxazolidin-2-one (264 mg, 0.57 mmol) and DCM (6 mL) and is cooled to −78° C. Boron tribromide (1M, 2.3 mL, 2.3 mmol) is then added dropwise, and after 30 min. the cooling bath is removed and the reaction is allowed to warm to room temperature. The reaction is quenched with water (5 mL), basified to pH 10 with 1N NaOH, and extracted with DCM. The combined organics are dried over Na2SO4, filtered, and concentrated. Purified on 40 g Redisep silica gel cartridge with 5% MeOH/DCM to give the title compound. 1H NMR (acetone-d6) δ 9.21 (s, 1H), 8.72 (dd, J=4.8, 1.7 Hz, 1H), 8.60 (br s, 1H), 8.36 (ddd, J=6.1, 1.9, 1.9 Hz, 1H), 7.58 (dd, J=8.0, 5.0, 0.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.27-7.22 (m, 3H), 6.95 (d, J=7.6 Hz, 1H), 6.92 (t, J=2.2 Hz, 1H), 6.82 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 5.67 (d, J=4.7 Hz, 1H), 5.50 (dd, J=14.7, 5.8 Hz, 1H), 5.42 (dd, J=14.7, 3.9 Hz, 1H), 5.12 (ddd, J=5.8, 4.6, 4.0 Hz, 1H), HPLC-MS calculated C22H17ClN6O3 (M+H+) 449.1, found 449.0.

Workup

  1. customafter 30 min. the cooling bath is removed
  2. temperatureto warm to room temperature
  3. customThe reaction is quenched with water (5 mL)
  4. extractionextracted with DCM
  5. dry with materialThe combined organics are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurified on 40 g Redisep silica gel cartridge with 5% MeOH/DCM

Sources & evidence

ORD record
ord-7b80a7e1891b4c469cf97dd7e2a3dc34
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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