Boron tribromide → HCID 25257694, compound

HRID 2046999Notes

Reaction equation

HRID 2046999 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20]C)[C:17]([O:22]C)=[C:16]([O:24]C)[CH:15]=3)=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([OH:20])[C:17]([OH:22])=[C:16]([OH:24])[CH:15]=3)=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole2×

Product 1

HCID 25257694HCID 25257694, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Phenyl-thiazol-4-yl)-(3,4,5-trihydroxy-phenyl)-methanone (11f) was synthesized beginning with compound 8f. To a solution of compound 8f (123 mg, 0.35 mmol) in 5 mL anh. CH2Cl2 was added BBr3 (1M solution in CH2Cl2, 1.75 mL, 5 mmol) under −78° C. The mixture was stirred for 2 h and a solution of amide 7 (1.14 mmol) in 3 mL THE was charged. The mixture was allowed to warm to room temperature slowly and stirred overnight. The reaction mixture was quenched with satd. NH4Cl, extracted with ethyl acetate, dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound as red crystalline solid. Yield: 50.9%. M.p. 175-176° C. 1H NMR (300 MHz, DMSO-d6) δ 8.44 (d, 1H), 8.07-8.04 (m, 2H), 7.57-7.55 (m, 3H), 7.33 (s, 2H). MS (ESI) m/z 336.1 [M+Na]+. Anal. (C6H11NO4S) C, H, N.

Workup

  1. stirringstirred overnight
  2. customThe reaction mixture was quenched with satd
  3. extractionNH4Cl, extracted with ethyl acetate
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customto yield a crude product, which

Sources & evidence

ORD record
ord-554d745b6acf44018c3974751cf94c6a
Source dataset
uspto-grants-2013_11
Patent number
US08592465B2

Reaction notes

Loading…