Boron tribromide → HCID 57991651, compound

HRID 556069Notes

Reaction equation

HRID 556069 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[O:23]C)=[N:10][C:9]=1[C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=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:25])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:23])=[N:10][C:9]=1[C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 57991601HCID 57991601, compound

Product 1

HCID 57991651HCID 57991651, compoundYield 67.1%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-2,4-dimethoxy-benzamide prepared in Example 35 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a white solid in a yield of 67.1%, mp: 217-219 └. 1H-NMR (400 Hz, Acetone-d6) δ: 4.40 (2H, s, CH2), 6.53 (1H, d, J=2.24 Hz, ArH), 6.58 (1H, dd, J=8.96 Hz, 2.24 Hz, ArH), 7.04 (2H, d, J=8.68 Hz, ArH), 7.32˜7.40 (5H, m, ArH), 7.65 (2H, d, J=8.68 Hz, ArH), 8.29 (1H, d, J=8.72 Hz, ArH); EI-MS m/e (%): 418.2 (M+, 33), 282.1 (100); HREI-MS Calcd. for C23H18N2O4S: 418.0987. found: 418.0970.

Workup

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

Sources & evidence

ORD record
ord-4b226b2a8b84435cb2131e5620c6c36f
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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