Boron tribromide → HCID 68815056, compound

HRID 731076Notes

Reaction equation

HRID 731076 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C: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]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[C: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 68814210HCID 68814210, compound

Product 1

HCID 68815056HCID 68815056, 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-4-(4-methoxy-phenyl)-3-methyl-2-phenyl-1H-indole (1.029 g, 2.550 mmol) was reacted with BBr3 (3.1 ml of a 1M solution in CH2Cl2) to give the product (0.657 g, 1.687 mmol, 66%) as a white solid, mp 174-176° C. 1H NMR (DMSO-d6) δ 1.73 (s, 3H), 5.28 (s, 2H), 6.79-6.82 (m, 3H), 6.88 (d, J=7.2 Hz, 2H), 7.07-7.10 (m, 1H), 7.15-7.19 (m, 1H), 7.20-7.23 (m, 4H), 7.28 (dd, J=0.8, 8.3 Hz, 1H), 7.32-7.34 (m, 2H), 7.39-7.47 (m, 3H), 9.41 (s, 1H); IR (solid) 3450, 3050, 1600, 1520, 1420, 1310, 1200 and 1180 cm−1; [ESI(+)], m/z 390 (M+H)+; Anal. Calcd. for C28H23NO: C, 86.34; H, 5.95; N, 3.60; Found: C, 86.13; H, 5.98; N, 3.56.

Sources & evidence

ORD record
ord-912e49e3e7b74302a9f8fc94d3eeca04
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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