Boron tribromide → HCID 136334111, compound

HRID 1593435Notes

Reaction equation

HRID 1593435 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:11]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C:25](=[O:29])[CH2:24][CH2:23]4)[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[C:11]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C:25](=[O:29])[CH2:24][CH2:23]4)[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 69429650HCID 69429650, compound

Product 1

HCID 136334111HCID 136334111, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of Step 4 (100 mg, 0.26 mmol) in dichloromethane (2 ml) was treated at 0° C. with boron tribromide (1.3 ml of a 1M solution in dichloromethane, 1.3 mmol) and stirred at room temperature for 1 hour. The reaction mixture was poured into saturated sodium bicarbonate solution extracted into dichoromethane, dried (Na2SO4) and concentrated in vacuo. The residue was dissolved in methanol/dichloromethane and applied to an SCX column eluting with methanol and then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo to afford the title compound (65 mg, 70%); MS(ES+) m/e 368 [M+H]+.

Workup

  1. extractionextracted into dichoromethane
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methanol/dichloromethane
  5. washeluting with methanol
  6. additiona mixture of 0.880 ammonia/methanol (1:9)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2880af9ef0b74b72bb195f452104b4c6
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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