Boron tribromide → HCID 46931462, compound

HRID 2361458Notes

Reaction equation

HRID 2361458 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]#[C:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([C:10]#[C:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 58362362HCID 58362362, compound

Product 1

HCID 46931462HCID 46931462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL round bottomed flask equipped with a magnetic stir bar containing DCM (5.2 mL) was placed 8 (0.08 g, 0.26 mmol). The reaction mixture was cooled to O° C. and BBr3 (0.75 mL of 1M in DCM) was added drop wise. The reaction was stirred at RT for 8 hr. The reaction was then neutralized with sat. NaHCO3 and extracted into DCM (2×10 mL). The combined organic extracts were washed with water (10 mL), brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified over silica gel using EtOAc:Hexanes (1:3) as the eluent to afford W366 (0.02 g, 26%) as a brown solid. 1H NMR (400 MHz, DMSO-d6), δ: 2.5 (d, J=10.4 Hz, 3H), 6.06-6.08 (m, 1H), 6.42 (t, J=8.8 Hz, 1H), 6.74 (dd, J=8.8, 2.4 Hz, 1H), 7.05-7.14 (m, 2H), 7.54 (d, J=8.8, 1H), 9.76 (br s, 1H); MS (ESI): 299.0 (M+H+).

Workup

  1. customTo a 25 mL round bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was cooled to O° C
  3. extractionextracted into DCM (2×10 mL)
  4. washThe combined organic extracts were washed with water (10 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified over silica gel
  8. customto afford W366 (0.02 g, 26%) as a brown solid

Sources & evidence

ORD record
ord-1a1a6f4f82d3499d93e3dd91ae2dd7bc
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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