Boron tribromide → HCID 57962607, compound

HRID 541908Notes

Reaction equation

HRID 541908 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[N:9][CH:10]=[C:11]([CH:25]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][C:15]=3[O:23]C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[N:9][CH:10]=[C:11]([CH:25]=3)[CH2:12][CH2:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][C:15]=3[OH:23]

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57962622HCID 57962622, compound

Product 1

HCID 57962607HCID 57962607, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into the reaction flask was added 6-chloro-12-methoxy-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene (1.35 g, 3.82 mmol), methylene chloride (20 mL), and 1.0 M of boron tribromide in methylene chloride (19.1 mL). The reaction mixture was stirred at rt overnight. To the mixture was added 1.0 M of sodium bicarbonate in water (30 mL). The precipitate formed was collected by vacuum filtration. The cake was washed with water and methylene chloride, and air dried to provide the desired product (1.25 g, 96%). LCMS for C17H15ClN5O (M+H)+: m/z=340.1.

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by vacuum filtration
  3. washThe cake was washed with water and methylene chloride, and air
  4. customdried

Sources & evidence

ORD record
ord-25dfab3759454bf2b53c2bc3d4dcafe4
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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