Boron tribromide → HCID 173244476, compound

HRID 394828Notes

Reaction equation

HRID 394828 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[C:11]1[C:12]2[NH:16][C:15]([C:17]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[C:18]3[N:41]=[C:21]([CH:22]=[C:23]4[NH:40][C:26](=[C:27]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:28]5[CH:29]=[CH:30][C:31]=1[N:32]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19]3)=[CH:14][CH:13]=2.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:11]1[C:12]2[NH:16][C:15]([C:17]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[C:18]3[N:41]=[C:21]([CH:22]=[C:23]4[NH:40][C:26](=[C:27]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:28]5[CH:29]=[CH:30][C:31]=1[N:32]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19]3)=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 173241704HCID 173241704, compound

Product 1

HCID 173244476HCID 173244476, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A starting compound (7)(20.5 mg, 31.9 μmol) was dissolved in 2 mL of chloroform. BBr3 (0.2 mL) was added by using a syringe under a nitrogen atmosphere. After stirred for 3 hours at room temperature, the resultant mixture was diluted by adding chloroform little by little to decompose excessive BBr3. The resultant solution was neutralized with an aqueous solution of sodium bicarbonate and then washed with water. After the solvent was removed, the resultant mixture was dried. As a result, the compound (8) (17.1 mg) was obtained in a yield of 87%.

Workup

  1. washwashed with water
  2. customAfter the solvent was removed
  3. dry with materialthe resultant mixture was dried

Sources & evidence

ORD record
ord-f5f5895a70804a03bd0997b7c4f3dd19
Source dataset
uspto-grants-2003_08
Patent number
US06602998B2

Reaction notes

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