Boron tribromide → HCID 20094644, compound

HRID 273920Notes

Reaction equation

HRID 273920 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]([CH2:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)[CH2:15][CH2:14][CH2:13][C:12]=3[C:11]([CH:29]=[O:30])=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]([CH2:18][C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)[CH2:15][CH2:14][CH2:13][C:12]=3[C:11]([CH:29]=[O:30])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20094648HCID 20094648, compound

Product 1

HCID 20094644HCID 20094644, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(4-Methoxyphenyl)-7-[(naphthyl)methyl]-4,5,6,7-tetrahydro-1H-indazole-3-carboxaldehyde (CP 325, 3.44 g, 8.68 mmol) and 26 mL of a 1.0M solution of BBr3 in CH2Cl2 (26 mmol) were combined and stirred at room temperature for 3 h. Additional CH2Cl2 was added and the solution was washed with water and brine. The mixture was concentrated and purified by MPLC using a solvent gradient ranging from 20-25% EtOAc:hexanes to give 0.40 g (12%) of the title compound as a white solid, m.p. >260° C.; 1H NMR (DMSO-d6, 300 MHz) 1.50 (m, 2H), 1.75 (m, 1H), 1.95 (m, 1H), 2.60 (m, 1H), 2.77 (t, 1H, J=12.7), 2.94 (broad d, 1H, J=13.6), 3.06 (broad d, 1H, J=10.8), 3.25 (m, 1H), 6.90 (d, 1H, J=8.5), 7.09 (d, 2H, J=8.7), 7.21 (d, 1H, J=6.5), 7.28 (t, 1H, J= 7.1), 7.4 (t, 1H, J=7.6), 7.47 (t, 1H J=7.4), 7.54 (d, 2H , J=8.7), 7.76 (d, 1H, J=8.2), 7.87 (d, 1H, J=7.9); IR (KBr) 3100 (broad), 1696, 1519 cm-1 ; MS (DCI) m/z 383 (base), 241. Anal. Calcd. for C26H26N2O2 : C, 78.63; H, 6.58; N, 7.03. Found: C, 78.23; H, 6.53; N, 6.99.

Workup

  1. washthe solution was washed with water and brine
  2. concentrationThe mixture was concentrated
  3. custompurified by MPLC

Sources & evidence

ORD record
ord-1f18241f4db04362ac3cab5987039a2e
Source dataset
uspto-grants-1995_02
Patent number
US05387693

Reaction notes

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