Boron tribromide → HCID 68814853, compound

HRID 731035Notes

Reaction equation

HRID 731035 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]([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]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)[C: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 68814868HCID 68814868, compound

Product 1

HCID 68814853HCID 68814853, 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-5-(4-methoxy-phenyl)-2,3-dimethyl-1H-indole (0.925 g, 2.709 mmol) was reacted with BBr3 (3.3 ml of a 1M solution in CH2Cl2) to give the product (0.608 g, 1.857 mmol, 69%) as a brown glass. 1H NMR (DMSO-d6) δ 2.23 (s, 3H), 2.27 (s, 3H), 5.38 (s, 2H), 6.81 (d, J=8.4 Hz, 2H), 6.98 (d, J=7.5 Hz, 2H), 7.19-7.23 (m, 2H), 7.27 (t, J=7.3 Hz, 2H), 7.34 (d, J=8.6 Hz, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.57 (s, 1H), 9.32 (s, 1H); [ESI(+)], m/z 328 (M+H)+.

Sources & evidence

ORD record
ord-138d64d90b9a40cfa20ece233904a101
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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