Boron tribromide → HCID 44124905, compound

HRID 1045369Notes

Reaction equation

HRID 1045369 reaction equation
C[O:2][CH2:3][C:4]1([C:21]([N:23]2[CH2:32][CH2:31][C:30]3[N:29]=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[CH:26][C:25]=3[CH2:24]2)=[O:22])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]=3[CH:20]=2)[CH2:5]1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][CH2:3][C:4]1([C:21]([N:23]2[CH2:32][CH2:31][C:30]3[N:29]=[CH:28][C:27]([C:33]([F:35])([F:36])[F:34])=[CH:26][C:25]=3[CH2:24]2)=[O:22])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16](=[O:18])[N:15]([CH3:19])[C:14]=3[CH:20]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 44124679HCID 44124679, compound

Product 1

HCID 44124905HCID 44124905, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound from Example 39 (770 mg, 1.52 mmol) in 14 mL of DCM at −78° C. was added a solution of BBr3 (4.58 mmol) in DCM. After 1 hour, the reaction mixture was warned up to −25° C. and the reaction was monitored by TLC. After completion, the mixture was quenched with sat. NaHCO3. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combinated organic layer were washed with brine, dried over MgSO4 and concentrated to gave the crude product, which was purified by a flash column chromatography give 172 mg of the title compound (0.351 mmol, 23%): 1H NMR (400 MHz, CD3OD): δ 8.63 (s, 1H), 7.89 (s, 1H), 7.20-7.15 (m, 3H), 4.83-4.79 (m, 2H), 4.15-3.85 (m, 2H), 3.81-3.60 (m, 2H), 3.40 (s, 2H), 3.35 (s, 3H), 3.30-3.00 (m, 3H), 2.80-2.60 (m, 3H), 2.32-2.20 (m, 1H), 2.10-1.99 (m, 1H); MS (ESI) m/z: Calculated for C24H25F3N4O4: 490.47. found 491.1 (M+H)+.

Workup

  1. customwas warned up to −25° C.
  2. customAfter completion, the mixture was quenched with sat. NaHCO3
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  5. washThe combinated organic layer were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto gave the crude product, which
  9. customwas purified by a flash column chromatography

Sources & evidence

ORD record
ord-f7c646c181f74dfdbcb5278f8e946cda
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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