Boron tribromide → HCID 22143669, compound

HRID 1825144Notes

Reaction equation

C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:14]([OH:16])=O)=[C:8]([CH3:13])[N:9]2[CH3:12])=[CH:5][CH:4]=1.B(Br)(Br)Br>>[CH:8]([NH:9][C:14]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([OH:2])=[CH:4][CH:5]=2)[N:9]([CH3:12])[C:8]=1[CH3:13])=[O:16])([CH3:13])[CH3:7]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 22143669HCID 22143669, compound

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid isopyropylamide 66a by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (300 MHz, CD3OD) δ 7.47 (1H, d, J=8.5 Hz), 6.74 (1H, d, J=2.1 Hz), 6.67 (1H, dd, J=2.1, 8.5 Hz), 4.22 (1H, m), 3.61 (3H, s), 2.56 (3H, s), 1.28 (3H, s), 1.26 (3H, s). LCMS (ESI+) [M+H]/z Calc'd 247. found 247.

Sources & evidence

ORD record: ord-7eed90fbce924d9781ccef41033894f4
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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