Boron tribromide → HCID 59644865, compound

HRID 646589Notes

Reaction equation

HRID 646589 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59215163HCID 59215163, compound

Product 1

HCID 59644865HCID 59644865, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-7-(3-methoxyphenyl)-[1,6]naphthyridine (0.052 g, 0.2 mmol) in dichloromethane (2 mL) was added boron tribromide (1 M solution in dichloromethane, 0.4 mL, 0.4 mmol) at −78° C. The resulting mixture was slowly warmed to room temperature. The residue was quenched with water and neutralized with aqueous sodium carbonate. The aqueous solution was then extracted with dichloromethane (2×30 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to give a tan oil. Purification by flash chromatography eluting with hexanes/EtOAc (1:1) afforded the title compound as a yellowish solid (0.040 g). 1H NMR (DMSO-d6, 400 MHz) δ 9.70 (b, 1H), 9.19 (dd, 1H), 8.54-8.64 (m, 1H), 8.37 (s, 1H), 7.77(dd, 1H), 7.64 (m, 2H), 7.32 (t, 1H), 6.87 (m, 1H); MS (m/e) calculated for C16H13ClN2O 256, found 257.5 (M+H).

Workup

  1. customThe residue was quenched with water and neutralized with aqueous sodium carbonate
  2. extractionThe aqueous solution was then extracted with dichloromethane (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a tan oil
  6. customPurification by flash chromatography
  7. washeluting with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-917111dafdce4731ac33c5fb4794d078
Source dataset
uspto-grants-2010_04
Patent number
US07705151B2

Reaction notes

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