Bromine → HCID 10168999, compound

HRID 1278808Notes

Reaction equation

HRID 1278808 reaction equation
[Br:1][C:2]1[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]=[C:4]([Br:24])[C:3]=1[OH:25].O[C@@H:27]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:28]([O-:30])=[O:29].BrBr>C(Cl)(Cl)Cl>[Br:24][C:4]1[CH:5]=[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:7]=[C:2]([Br:1])[C:3]=1[O:25][C@H:27]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 24408BromineHCID 9893519HCID 9893519, compoundHCID 40501121HCID 40501121, compound

Product 1

HCID 10168999HCID 10168999, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from 2,6-dibromo-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (Example 9) and (S)-2-hydroxy-4-phenyl-butyrate, ethyl ester (Example 27) according to the procedure of Example 30. White solid: [a]25/D =−12.187° (9.929 mg/mL, CHCl3); NMR (DMSO-d6); δ 13.24 (s, 1H), 8.21 (d, J=8 Hz, 1H), 7.73 (s, 2H), 7.67 (ddd, J=8, 7, 1 Hz, 1H), 7.52-7.45 (m, 2H), 7.32-7.28 (m, 2H), 7.24-7.20 (m, 3H) 5.02 (d, J=6Hz, 1H), 2.99-2.86 (m, 1H), 2.75-2.65 (m, 1H), 2.45 (s, 3H), 2.30-2.20 (m, 2H), 1.61 (s, 3H); MS (+FAB): [M+], 3 bromine isotope pattern, 700 (30%), 702 (100%), 704 (90%), 706 (55%); Anal. Calc. for C30H23Br3O3S: C, 51.23, H, 3.30, N, 0.00. Found: C, 51.33, H, 3.33, N, 0.29.

Sources & evidence

ORD record
ord-b475d63f557d405eab4176e75035523b
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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