Methyl 2-bromopropionate → HCID 12192068, compound

HRID 1184432Notes

Reaction equation

HRID 1184432 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([N+:13]([O-])=O)[CH:7]=1)(=[O:5])=[O:4])[CH3:2].Br[CH:17]([CH3:22])[C:18](OC)=[O:19]>>[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]2[O:12][CH:17]([CH3:22])[C:18](=[O:19])[NH:13][C:8]=2[CH:7]=1)(=[O:5])=[O:4])[CH3:2]

Participants

3

Reactant 2

HCID 95576Methyl 2-bromopropionateHCID 30202754-(Ethylsulphonyl)-2-nitrophenol

Product 1

HCID 12192068HCID 12192068, compound

Procedure

Using 4-(ethylsulfonyl)-2-nitrophenol and methyl 2-bromopropanoate in the general procedure for alkylation of substituted-2-nitrophenols followed by reaction of the product in the general procedure for reduction of nitro group and subsequent ring closure gives a white solid: 1H NMR (DMSO-d6, 400 MHz): δ=10.96 (s, 1H), 7.43 (dd, J=8.3, 2.0 Hz, 1H), 7.37 (d, J=2.3 Hz, 1H), 7.19 (d, J=8.3 Hz, 1H), 4.85 (q, J=6.8 Hz, 1H), 3.23 (q, J=7.3 Hz, 2H), 1.46 (d, J=6.8 Hz, 3H), 1.10 ppm (t, J=7.5 Hz, 3H). ESI-MS: m/z 256.1 (M+H)+.

Workup

  1. customfollowed by reaction of the product in the general procedure for reduction of nitro group and subsequent ring closure
  2. customgives a white solid

Sources & evidence

ORD record
ord-c159141a94fd420c9d4a9bf85facea30
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

Loading…