Boron tribromide → HCID 18976157, compound

HRID 2393600Notes

Reaction equation

HRID 2393600 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]2([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:19]2=[O:32])=[O:16])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9](/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]2([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:19]2=[O:32])=[O:16])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18976190HCID 18976190, compound

Product 1

HCID 18976157HCID 18976157, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, 2 ml of boron tribromide was added dropwise to a stirred solution of 1.64 g of ethyl 3-[2,3-dihydro-3-[(E)-3-(3-methoxyphenyl)-2-propenoylamino]-2-oxo-1-pentyl-1H-indol-3-yl]propionate in methylene chloride (30 ml). After stirring under ice cooling for 1 hour, the mixture was poured into ice water and extracted with chloroform. After the extract was dried, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography [hexane-ethyl acetate (1:1)] to afford 1.53 g of ethyl 3-[2,3-dihydro-3-[(E)-3-(3-hydroxyphenyl)-2-propenoylamino]-2-oxo-1-pentyl-1H-indol-3-yl]propionate as a colorless amorphous solid. IR (Nujol) (cm-1) : 3280, 1705, 1660, 1610, FAB-MS (m/z): 465 (MH+), 302, 256, 228, 147 (base).

Workup

  1. extractionextracted with chloroform
  2. customAfter the extract was dried
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography [hexane-ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-d0cb5a6cebe74dbf99661b483452d7ab
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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