Dimethyl Ether → HCID 18455681, compound

HRID 1272450Notes

Reaction equation

HRID 1272450 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25]C.COC.B(Br)(Br)Br>>[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][C:17]([NH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:27]

Participants

4

Reactant 3

HCID 8254Dimethyl EtherHCID 25134Boron tribromideHCID 18455774HCID 18455774, compound

Product 1

HCID 18455681HCID 18455681, compoundYield 32%

Procedure

The product was prepared from N-[2-(1H-Indol-2-yl)-phenyl]-2-(2-methoxy-phenyl)-acetamide. Cleavage of the methylether was accomplished using 1.8 eq of BBr3 (1M solution in dichloromethane) at −78° C. to room temperature (23° C.) and subsequent hydrolysis (32% yield). 96% Purity by HPLC (ELSD), Mass-spec [M+H+]=343, 1H NMR (MeOH-d4): 3.69 s (2H), 6.25 s (1H), 6.71–6.74 m (2H), 7.01–7.07 m (2H), 7.10–7.13 m (2H), 7.22 t, 7 Hz (1H), 7.31–7.36 m (2H), 7.48 d, 8 Hz (1H), 7.52 dd, 8.1 Hz (1H), 8.08 d, 8 Hz (1H).

Workup

  1. customat −78° C. to room temperature
  2. custom(23° C.) and subsequent hydrolysis (32% yield)

Sources & evidence

ORD record
ord-f1744ffd613c4ec698915089897bb71e
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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