Bromine → HCID 21970365, compound

HRID 1873174Notes

Reaction equation

HRID 1873174 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:31])[C:3]=1[OH:32].O[C@@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([O:37]C)=[O:36].BrBr>>[Br:31][C:4]1[CH:5]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:7]=[C:2]([Br:1])[C:3]=1[O:32][C@H:34]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:35]([OH:37])=[O:36]

Participants

4

Reactant 3

HCID 24408BromineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18687853HCID 18687853, compound

Product 1

HCID 21970365HCID 21970365, compound

Procedure

Prepared from of 2,6-dibromo-4-[6-(2-dimethylamino-ethylsulfanyl)-benzo [b]naphtho[2,3-d]thiophen-11-yl]-phenol (Example 66) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 169-174° C.; NMR (DMSO-d6); δ13.3 (broad s, 1 H), 8.64 (d, J=8 Hz, 1 H), 8.04 (d, J=8 Hz, 1 H), 7.81 (ddd, J=8,7,1 Hz, 1 H), 7.76 (dd, J=16,1 Hz), 7.72-7.48 (m, 4 H), 7.42-7.22 (m, 7 H), 6.64 (d, J=8 Hz, 1 H), 5.32 (t, J=7 Hz, 1 H), 3.36-3.14 (m, 6 H); 2.64 (s, 6 H); MS (+FAB): [(M+H)+], 2 bromine isotope pattern, 734-(55%), 736 (100%), 738 (70%). Anal. calc. for C35H29Br2NO3S2; C, 54.45, H, 3.92, N, 1.81. Found: C, 54.46, H, 3.76, N, 1.66.

Sources & evidence

ORD record
ord-c90f72fde1b5480bbdb2775e575b783f
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…