Boron tribromide → HCID 12992346, compound

HRID 354092Notes

Reaction equation

HRID 354092 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:28]3[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:36]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[C:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:17][CH:18]=3)=[O:12])=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:36]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12992345HCID 12992345, compound

Product 1

HCID 12992346HCID 12992346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step 4 (120 mg, 0.24 mmol) was dissolved in methylene chloride (0.5 mL), cooled to 0° C. and treated with boron tribromide (1.2 mL, 1 M, 1.2 mmol) and stirred for 30 minutes. The reaction was quenched with saturated sodium bicarbonate solution and extracted intochloroform. The combined organic layers was dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography with 2% methanol-methylene chloride as eluant the title compound (24 mg) was obtained.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  2. extractionextracted intochloroform
  3. dry with materialThe combined organic layers was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration, concentration and silica gel column chromatography with 2% methanol-methylene chloride as eluant the title compound (24 mg)
  5. customwas obtained

Sources & evidence

ORD record
ord-f957c483321b45edb6687fe9d59d7655
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

Loading…