Boron tribromide → HCID 68813921, compound

HRID 731111Notes

Reaction equation

HRID 731111 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[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]([C: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)[N: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 68814892HCID 68814892, compound

Product 1

HCID 68813921HCID 68813921, 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-methyl-2-phenyl-1H-indole (0.757 g, 1.876 mmol) was reacted with BBr3 (2.3 ml of a 1M solution in CH2Cl2) to give the product (0.371 g, 0.953 mmol, 51%) as a solid, mp 133-135° C. 1H NMR (DMSO-d6) δ 3.61 (s, 3H), 4.03 (s, 2H), 6.80 (d, J=8.6 Hz, 2H), 7.07-7.10 (m, 3H), 7.18 (t, J=7.9 Hz, 2H), 7.38-7.39 (m, 3H), 7.44-7.55 (m, 7H), 9.36 (s, 1H); IR (solid) 3290, 3020, 1605, 1520, 1480, 1430, 1370, and 1230 cm−1; [ESI(+)], m/z 390 (M+H)+; Anal. Calcd. for C28H23NO-0.25H2O: C, 85.36; H, 6.01; N, 3.55; Found: C, 85.52, H, 5.94; N, 3.32.

Sources & evidence

ORD record
ord-9bc070206e9c4e4bb1f15154553fbb03
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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