Boron tribromide → HCID 68814298, compound

HRID 731104Notes

Reaction equation

HRID 731104 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:9]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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][C:13]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:9]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68814335HCID 68814335, compound

Product 1

HCID 68814298HCID 68814298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 1,3-dibenzyl-5-(4-methoxy-phenyl)-2-phenyl-1H-indole (1.162 g, 2.423 mmol) was reacted with BBr3 (2.9 ml of a 1M solution in CH2Cl2) to give the product (1.105 g, 2.373 mmol, 98%) as a brown oil. 1H NMR (DMSO-d6) δ 4.05 (s, 2H), 5.33 (s, 2H), 6.79 (d, J=8.6 Hz, 2H), 6.87 (d, J=7.5 Hz, 2H), 7.08-7.23 (m, 8H), 7.30 (d, J=8.4 Hz, 1H), 7.35-7.40 (m, 5H), 7.42-7.49 (m, 3H), 7.52 (s, 1H), 9.36 (s, 1H); [ESI(+)], m/z 466 (M+H)+.

Sources & evidence

ORD record
ord-33fd7666c46d44e6a9108cf50b8ecceb
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…