Boron tribromide → HCID 67312067, compound

HRID 1400588Notes

Reaction equation

HRID 1400588 reaction equation
C[O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH3:17])[C:10]3[CH2:24][CH2:25][N:26]([CH3:28])[CH2:27][C:9]=3[C:8]=2[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl.C(=O)=O>[CH3:28][N:26]1[CH2:25][CH2:24][C:10]2[N:11]([CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH3:17])[C:12]3[CH:13]=[CH:14][C:6]([NH:5][CH2:4][CH2:3][OH:2])=[CH:7][C:8]=3[C:9]=2[CH2:27]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 67310986HCID 67310986, compound

Product 1

HCID 67312067HCID 67312067, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2-Methoxy-ethyl)-[2-methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl]-amine (350 mg, 0.9 mmol) was dissolved in DCM and the reaction mixture was cooled in dry ice (−78° C.). Boron tribromide (699 mg, 2.7 mmol), diluted with DCM (3 mL) was added to the solution dropwise at −78° C. After completion of this addition, the reaction mixture was allowed to come to RT gradually, and was stirred at RT for 1 h. After completion of reaction (reaction monitored by TLC & LCMS), the reaction mixture was concentrated under vacuum and the crude compound was basified with 1N NaOH solution. The compound was extracted with EtOAc (3×60 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum under vacuum to obtain the crude compound which was recrystallized in diethyl ether (20 mL) to yield 170 mg of 2-[2-Methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-ylamino]-ethanol. 1H NMR (CD3OD, HCl salt) δ (ppm): 8.90 (d, 2H), 8.40 (d, 2H), 7.84 (s, 1H), 7.78 (s, 1H), 7.52 (d, 1H), 7.42 (d, 1H), 4.84 (m, 1H), 4.50 (m, 1H), 3.90 (m, 1H), 3.80 (t, 2H), 3.68 (m, 1H), 3.58 (t, 2H), 3.40-3.30 (m, 2H), 3.18 (s, 3H), 2.17 (s, 3H).

Workup

  1. additionwas added to the solution dropwise at −78° C
  2. additionAfter completion of this addition
  3. customto come to RT
  4. customAfter completion of reaction (reaction monitored by TLC & LCMS)
  5. concentrationthe reaction mixture was concentrated under vacuum
  6. extractionThe compound was extracted with EtOAc (3×60 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated under vacuum under vacuum
  9. customto obtain the crude compound which
  10. customwas recrystallized in diethyl ether (20 mL)

Sources & evidence

ORD record
ord-1d7cbfa0906f4249a21713e5f01e9d44
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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