Boron tribromide → HCID 68814272, compound

HRID 731097Notes

Reaction equation

HRID 731097 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]3[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)=[CH:17][CH:16]=2)[C:12]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:13]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68813801HCID 68813801, compound

Product 1

HCID 68814272HCID 68814272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 5-(4-methoxy-phenyl)-1-methyl-3-pentyl-2-phenyl-1H-indole (0.505 g, 1.317 mmol) was reacted with BBr3 (1.6 ml of a 1M solution in CH2Cl2) to give the product (0.375 g, 1.023 mmol, 78%) as a light-brown oil. 1H NMR (DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.14-1.22 (m, 4H), 1.51-1.57 (m, 2H), 2.65 (t, J=7.5 Hz, 2H), 3.55 (s, 3H), 6.84 (d, J=8.6 Hz, 2H), 7.39 (dd, J=1.7, 8.4 Hz, 1H), 7.43-7.50 (m, 6H), 7.54 (t, J=7.2 Hz, 2H), 7.68 (d, J=1.5 Hz, 1H), 9.37 (s, 1H); [ESI(+)], m/z 370 (M+H)+.

Sources & evidence

ORD record
ord-b9f2bd70fe0d431b90389094e7b3832a
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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