2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one → HCID 71536350, compound

HRID 1519291Notes

Reaction equation

HRID 1519291 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].Br[CH2:24][C:25]([C:27]1[CH:36]=[CH:35][C:30]2[O:31][CH2:32][CH2:33][O:34][C:29]=2[CH:28]=1)=O>>[O:31]1[C:30]2[CH:35]=[CH:36][C:27]([C:25]3[N:12]=[C:11]([C:9]4[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=5[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=4)[S:13][CH:24]=3)=[CH:28][C:29]=2[O:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 27761712-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-oneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536350HCID 71536350, compoundYield 71%

Procedure

4-[4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (205 mg, 71%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one (available from Alfa Aesar) using the procedure described for the preparation of Example 1. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (d, J=1.8 Hz, 2H), 8.24 (dd, J=8.0, 1.9 Hz, 1H), 8.11-8.16 (m, 2H), 7.78 (t, J=7.8 Hz, 1H), 7.52-7.68 (m, 3H), 7.43 (t, J=8.0 Hz, 2H), 6.95 (d, J=9.0 Hz, 1H), 4.29 (s, 4H).

Workup

  1. customdescribed for the preparation of Example 1

Sources & evidence

ORD record
ord-e01efceca2864d5f8b44874a19392e88
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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