Boron tribromide → HCID 68814801, compound

HRID 731062Notes

Reaction equation

HRID 731062 reaction equation
[CH2:1]([C: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)[N:10]([CH3:25])[C:9]=1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[CH:15]=2)[N:10]([CH3:25])[C:9]=1[CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68814959HCID 68814959, compound

Product 1

HCID 68814801HCID 68814801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 3-benzyl-5-(4-methoxy-phenyl)-1,2-dimethyl-1H-indole (0.419 g, 1.227 mmol) was reacted with BBr3 (1.5 ml of a 1M solution in CH2Cl2) to give the product (0.329 g, 1.004 mmol, 82%) as an off-white solid, dec. 129-133° C. 1H NMR (DMSO-d6) δ 2.35 (s, 3H), 3.62 (s, 3H), 4.01 (s, 2H), 6.75 (d, J=8.7 Hz, 2H), 7.04-7.09 (m, 1H), 7.15-7.22 (m, 5H), 7.31-7.37 (m, 3H), 7.47 (d, J=1.5 Hz, 1H), 9.27 (s, 1H): [ESI(+)], m/z 328 (M+H)+.

Sources & evidence

ORD record
ord-cc13786785c14ea9b5c71f71e648ee68
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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