Boron tribromide → N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dihydroxy-benzamide

HRID 556062Notes

Reaction equation

HRID 556062 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([O:31]C)=[C:27]([O:33]C)[CH:26]=3)[S:11][C:12]=2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([OH:33])[CH:26]=3)[S:11][C:12]=2[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 57991645N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide

Product 1

HCID 57991588N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dihydroxy-benzamideYield 63.3%

Procedure

A procedure similar to that in Example 7 was used. N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 20 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a pale yellow solid in a yield of 63.3%, mp: 276-278 └(Dec). 1H-NMR (DMSO-d6, 400 MHz) δ: 4.41 (2H, s, CH2), 6.81 (1H, d, J=8.12 Hz, ArH), 7.29 (2H, t, 3JFH=3JHH=8.96 Hz, ArH), 7.47˜7.54 (4H, m, ArH), 7.67 (2H, dd, 3JHH=8.68 Hz, 4JFH=5.60 Hz, ArH), 8.20 (2H, d, J=8.40 Hz, ArH), 9.32 (1H, br, OH), 9.81 (1H, br, OH), 12.38 (1H, br, CONH); EI-MS m/e (%): 465.0 (M+, 28), 329.0 (100); HREI-MS Calcd. for C23H16FN3O5S: 465.0795. found: 465.0798.

Workup

  1. customThe obtained crude product
  2. customwas recrystallized with acetone

Sources & evidence

ORD record
ord-821a13445c9545479105ebfe69e7d2b3
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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