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

HRID 556107Notes

Reaction equation

[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:27])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[C:19]([O:25]C)[CH:18]=2)=[N:10][C:9]=1[C:28]1[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:27])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([OH:25])[CH:18]=2)=[N:10][C:9]=1[C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57991640HCID 57991640, compound

Product 1

HCID 57991630N-[5-benzyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3-(3,4-dihydroxy-phenyl)-propanamideYield 60.3%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3-(3,4-dimethoxy-phenyl)-propanamide prepared in Example 68 and boron tribromide were used as starting materials, and the crude product was recrystallized with ethyl acetate to obtain a product as a white solid in a yield of 60.3%, mp: 94-95 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.61 (2H, t, J=7.00 Hz, CH2), 2.68 (2H, t, J=7.00 Hz, CH2), 4.17 (2H, s, CH2), 6.43 (1H, d, J=7.84 Hz, ArH), 6.59 (2H, t, J=7.84 Hz, CH2), 6.80 (2H, d, J=7.84 Hz, ArH), 7.18˜7.24 (3H, m, ArH), 7.32 (2H, t, J=7.28 Hz, CH2), 7.41 (2H, d, J=7.84 Hz, ArH), 8.65 (1H, s, OH), 8.74 (1H, s, OH), 9.59 (1H, s, OH), 12.06 (1H, s, CONH); EI-MS m/e (%): 446.1 (M+, 18), 282.1 (100), 205.1 (17); HREI-MS Calcd. for C25H22N2O4S: 446.1300. found: 446.1299.

Workup

customthe crude product was recrystallized with ethyl acetate

Sources & evidence

ORD record: ord-86e97b6f65a44d00ba24d06c54b47430
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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