Bromine → HCID 22665454, compound

HRID 1278812Notes

Reaction equation

[Br:1][C:2]1([N+:25]([O-:27])=[O:26])[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([Br:23])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[CH:4][CH:3]1[OH:24].O[C@@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32]C)=[O:31].BrBr>>[Br:1][C:2]1([N+:25]([O-:27])=[O:26])[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([Br:23])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[CH:4][CH:3]1[O:24][CH:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

Reactant 3

HCID 24408Bromine

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoate

HCID 22665456HCID 22665456, compound

Product 1

HCID 22665454HCID 22665454, compound

Procedure

Prepared from of 2-bromo-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-nitro-phenol (Example 21) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 25) according to the procedure of Example 30. White solid: mp 243-245° C.: NMR (DMSO-d6); δ 11.30 (broad s, 1H), 8.23, 8.22 (2d, J=3 Hz, 1H), 8.06, 8.04 (2d, J=3 Hz, 1H), 7.95 (t, J=2, 1H), 7.68 (m, 1H), 7.56-7.50 (m, 1H), 7.45 (d, J=8 Hz, 1H),7.34-7.24 (m, 6H), 5.28 5.22 (2t, J=6Hz, 1H), 3.40-3.23 (m, 2H), 4.82 (d, J=6 Hz, 1H), 2.46 (s, 3H), 1.59 1.57 (2s, 3H); MS (+FAB): 2 bromine isotope pattern 653, 655 , 657; Anal. Calc. for C29H21Br2NO5S: C, 53.15, H, 3.23, N, 2.14. Found: C, 53.77, H, 3.73, N, 2.04.

Sources & evidence

ORD record: ord-da74a70a2b2d47578431d1482b4f2a9c
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444670B2

Reaction notes

Loading…