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

HRID 556064Notes

Reaction equation

[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[S:11][C:10]([NH:12][C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([O:22]C)[CH:15]=3)=[N:9][C:8]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[S:11][C:10]([NH:12][C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:22])[CH:15]=3)=[N:9][C:8]=2[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:33][CH:34]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86636629HCID 86636629, compound

Product 1

HCID 57991643N-[5-(4-fluoro-benzyl)-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4-dihydroxy-benzamideYield 64.4%

Procedure

A procedure similar to that in Example 7 was used. N-[5-(4-fluoro-benzyl)-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 30 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product of while solid in a yield of 64.4%, mp: 154-155└. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.19 (2H, s, CH2), 6.80˜6.86 (3H, m, ArH), 7.15 (2H, t, 3JFH=3JHH=9.00 HZ, ArH), 7.27 (2H, dd, 3JHH=8.72 Hz, 4JFH=5.64 Hz, ArH), 7.43˜7.56 (4H, m, ArH), 12.25 (1H, br, CONH); EI-MS m/e (%): 436.1 (M, 24), 300.1 (100); HREI-MS Calcd. for C23H17FN2O4S: 436.0893. found: 436.0900.

Workup

customThe obtained crude product
customwas recrystallized with acetone
customto give a product of while solid in a yield of 64.4%, mp

Sources & evidence

ORD record: ord-e43c6e827509435a9b4f7763d0eeb5f7
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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