Boron tribromide → HCID 68814952, compound

HRID 731055Notes

Reaction equation

HRID 731055 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[CH3:32])[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:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:9]1[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68815903HCID 68815903, compound

Product 1

HCID 68814952HCID 68814952, 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-methyl-1H-indole (0.692 g, 1.657 mmol) was reacted with BBr3 (2.0 ml of a 1M solution in CH2Cl2) to give the product (0.347 g, 0.860 mmol, 52%) as an off-white solid, mp 170-171° C. 1H NMR (DMSO-d6) δ 2.34 (s, 3H), 4.09 (s, 2H), 5.41 (s, 2H), 6.79 (d, J=8.5 Hz, 2H), 6.98 (d, J=7.3 Hz, 2H), 7.09-7.14 (m, 1H), 7.20-7.23 (m, 6H), 7.28 (t, J=7.1 Hz, 2H), 7.35-7.38 (m, 3H), 7.52 (d, J=1.3 Hz, 1H), 9.31 (s, 1H); IR (solid) 3530, 3020, 1600, 1480, 1260 and 11180 cm−1; [ESI(+)], m/z 404 (M+H)+; Anal. Calcd. for C29H25NO: C, 86.32; H, 6.24; N, 3.47; Found: C, 86.30; H, 5.99; N, 3.09.

Sources & evidence

ORD record
ord-08f5d6ecb26a4c3fbea7ad6715f956d7
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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