Boron tribromide → HCID 178448492, compound

HRID 254638Notes

Reaction equation

HRID 254638 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[S:7]/[C:6]/1=[N:14]\[C:15]([C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24]C)=[S:16])[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:10]([C:8]1[S:7]/[C:6](=[N:14]\[C:15](=[S:16])[C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[OH:24])/[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:9]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 178448493HCID 178448493, compound

Product 1

HCID 178448492HCID 178448492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 6C (212 mg, 0.534 mmol) in CH2Cl2 (20 mL) at 0° C. was added IM BBr3 in CH2Cl2 (1.6 mL, 1.6 mmol) and the reaction was allowed to warm to room temperature for 3 h. Saturated sodium bicarbonate was added, and the organic layer was separated, washed with brine, dried with anhydrous MgSO4 and concentrated under reduced pressure to provide quantitatively of the title compound. 1H NMR (300 MHz-DMSO-d6) δ: 0.95 (t, J=7 Hz, 4H), 1.37 (s+m, 11H), 1.82 (m, 2H), 4.30 (t, J=7 Hz, 2H), 6.95 (d, J=9 Hz, 1H), 7.40 (d-d, J=9 Hz, 3 Hz, 1H), 7.80 (s, 1H), 8.37 (d, J=3 Hz, 1H), 13.62 (s, 1H); MS (DCI/NH3) m/z 383 (M+H)+.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried with anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff827df49706432fbf1eef9d39c5e290
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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