Boron tribromide → HCID 68814691, compound

HRID 731069Notes

Reaction equation

HRID 731069 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[CH:15]=2)[C:10]([CH3:25])=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:15]=2)[C:10]([CH3:25])=[C:9]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68814367HCID 68814367, compound

Product 1

HCID 68814691HCID 68814691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 1-benzyl-6-(4-methoxy-phenyl)-3-methyl-2-phenyl-1H-indole (1.017 g, 2.861 mmol) was reacted with BBr3 (3.4 ml of a 1M solution in CH2Cl2) to give the product (0.726 g, 1.864 mmol, 65%) as a white solid, mp 141-143° C. 1H NMR (DMSO-d6) δ 2.23 (s, 3H), 5.37 (s, 2H), 6.80 (d, J=8.6 Hz, 2H), 6.85 (d, J=7.2 Hz, 2H), 7.13 (t, J=7.3 Hz, 1H), 7.18 (t, J=7.0 Hz, 2H), 7.30 (dd, J=1.5, 8.3 Hz, 1H), 7.38-7.49 (m, 7H), 7.51 (d, J=0.9 Hz, 1H), 7.58 (d, J=8.1 Hz, 1H), 9.40 (s, 1H); IR (solid) 3300, 3030, 1600, 1520, 1450, 1350, 1260, 1230 and 1180 m−1; [ESI(+)], m/z 390 (M+H)+; Anal. Calcd. for C28H23NO: C, 86.34; H, 5.95; N, 3.60; Found: C, 85.88; H, 6.21; N, 3.36.

Sources & evidence

ORD record
ord-c390c53b919647ceaae42bb203828c8d
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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