Boron tribromide → HCID 59161229, compound

HRID 545514Notes

Reaction equation

HRID 545514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22]C)[C:10]1[CH2:9][CH2:8][CH:7]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:6][C:5]2=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])[C:10]1[CH2:9][CH2:8][CH:7]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67196879HCID 67196879, compound

Product 1

HCID 59161229HCID 59161229, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve N-[6-chloro-9-(2-methoxy-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 19) (100 mg, 0.24 mmol) in anhydrous dichloromethane (3 mL) under nitrogen and cool in a brine/ice bath to 0° C. Slowly add boron tribromide (1M in dichloromethane, 1.22 mL, 1.22 mmol). After 30 min remove the ice bath and allow to warm to ambient temperature over 4 h. Dilute with ethyl acetate (12 mL) and wash with water. Extract aqueous portion with ethyl acetate (3×). Combine all organic portions, wash with water, brine, dry (MgSO4), and concentrate in vacuo to obtain a residue. Elute the residue over a silica pad with 25% ethyl acetate/dichloromethane to obtain 93 mg (96%) of a tan solid. MS (ES): m/z 397, 399 (M+1), 395, 397 (M−1); 1H NMR(DMSO-d6): δ 9.83 (s, 1H), 7.85 (d, 1H, J=7.9 Hz), 7.45 (s, 1H), 7.33 (d, 1H, J=8.4 Hz), 7.04 (m, 2H), 6.86 (d, 1H, J=7.9 Hz), 6.63 (t, 1H, J=7.3 Hz), 6.32 (d, 1H, J=7.5 Hz), 5.23 (s, 2H), 4.02 (m, 1H), 2.95 (dd, 1H, J=15.2, 5.1 Hz), 2.84-2.66 (m, 2H), 2.52 (m, 1H), 2.40 (m, 1H), 1.97 (m, 1H), 1.80 (m, 1H), 1.02 (m, 7H).

Workup

  1. customAfter 30 min remove the ice bath
  2. temperatureto warm to ambient temperature over 4 h
  3. additionDilute with ethyl acetate (12 mL)
  4. washwash with water
  5. washCombine all organic portions, wash with water, brine
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue
  9. washElute the residue over a silica pad with 25% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-d973ba865b5042f38017349306d91a37
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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