2-Bromo-1,3,2-benzodioxaborole → HCID 178517739, compound

HRID 474812Notes

Reaction equation

HRID 474812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][C:25]4[CH:26]=[N:27][C:28]([O:31]C)=[N:29][CH:30]=4)[C:21](=[O:23])[N:22]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].B1(Br)OC2C(=CC=CC=2)O1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][S:16][C:17]3[NH:18][CH:19]=[C:20]([CH2:24][C:25]4[CH:30]=[N:29][C:28](=[O:31])[NH:27][CH:26]=4)[C:21](=[O:23])[N:22]=3)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:33]([F:35])([F:36])[F:34]

Participants

4

Reactant 2

HCID 35523842-Bromo-1,3,2-benzodioxaboroleHCID 178494155HCID 178494155, compound

Product 1

HCID 178517739HCID 178517739, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-{[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]thio}-5-{[2-(methyloxy)-5-pyrimidinyl]methyl}-4(1H)-pyrimidinone and B-bromocatecholborane (357 mg, 1.795 mmol) in DCM (10 mL) was stirred at room temperature for 24 h. Purification via MDAP then afforded the title compound (24 mg, 25.3% yield). LCMS: rt=3.01 min, [M+H+]=521

Workup

  1. customPurification via MDAP

Sources & evidence

ORD record
ord-da05125e9f134773988fbe0fd9f62e46
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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