2-Bromo-4'-methylacetophenone → HCID 71536080, compound

HRID 1519298Notes

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:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)=O>>[N+:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]2[S:13][CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[N:12]=2)=[CH:8][CH:7]=1)([O-:22])=[O:21]

Participants

Reactant 2

HCID 692722-Bromo-4'-methylacetophenone

HCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536080HCID 71536080, compoundYield 32%

Procedure

2′-Nitro-4-(4-p-tolyl-thiazol-2-yl)-biphenyl-2-carboxylic acid (85 mg, 32%) 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-4′-methylacetophenone (available from ASDI Incorporated) using the procedure described for the preparation of Example 39. 1H NMR (400 MHz, DMSO-d6) δ 13.15 (br s, 1H), 8.57 (d, J=1.9 Hz, 2H), 8.26 (dd, J=8.0, 1.9 Hz, 1H), 8.20 (s, 1H), 8.15 (dd, J=8.1, 0.9 Hz, 1H), 7.97 (d, J=8.1 Hz, 2H), 7.77-7.82 (m, 1H), 7.63-7.69 (m, 1H), 7.42-7.48 (m, 2H), 7.30 (d, J=8.0 Hz, 2H), 2.36 (s, 3H).

Workup

customdescribed for the preparation of Example 39

Sources & evidence

ORD record: ord-25829f063ea7488eb1c5e560e3cf253a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

Loading…