Boron tribromide → HCID 57991603, compound

HRID 556076Notes

Reaction equation

HRID 556076 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[C:19]([O:21]C)[CH:18]=[C:17]([O:23]C)[CH:16]=2)=[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]=[C:19]([OH:21])[CH:18]=[C:17]([OH:23])[CH:16]=2)=[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 57991577HCID 57991577, compound

Product 1

HCID 57991603HCID 57991603, compoundYield 48.2%

Procedure

A procedure similar to that in Example 7 was used. N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,5-dimethoxy-benzamide prepared in Example 43 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 48.2%, mp: 262-263 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.21 (2H, s, CH2), 6.44 (1H, t, J=2.12 Hz, ArH), 6.83 (2H, d, J=8.40 Hz, ArH), 6.88 (2H, d, J=2.24 Hz, ArH), 7.22˜7.26 (3H, m, ArH), 7.32˜7.35 (2H, m, ArH), 7.46 (2H, d, J=8.68 Hz, ArH), 9.52 (2H, br, OH), 12.39 (1H, br, CONH); EI-MS m/e (%): 418.1 (M+, 82), 282.1 (66), 137.0 (100); HREI-MS Calcd. for C23H18N2O4S: 418.0987. found: 418.0981.

Workup

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

Sources & evidence

ORD record
ord-45884858e76645d5b37a2f3b4d9bd3dc
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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