Boron tribromide → HCID 59596250, compound

HRID 2264774Notes

Reaction equation

HRID 2264774 reaction equation
B(Br)(Br)Br.ClC1N(C)N=C(C)C=1S([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2([C:33]3[CH:38]=[C:37]([Cl:39])[N:36]=[C:35]([Cl:40])[CH:34]=3)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([NH2:32])=[N:24]2)[CH:18]=1)(=O)=O>ClCCl>[NH2:32][C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([C:19]2[CH:18]=[C:17]([OH:16])[CH:22]=[CH:21][CH:20]=2)([C:33]2[CH:34]=[C:35]([Cl:40])[N:36]=[C:37]([Cl:39])[CH:38]=2)[N:24]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24874863HCID 24874863, compound

Product 1

HCID 59596250HCID 59596250, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.229 mL, 2.42 mmol) was added to a solution of 1-(2,6-dichloropyridin-4-yl)-1-(3-methoxyphenyl)-1H-isoindol-3-amine (Scheme #19, C, 0.62 g, 1.61 mmol) in dry dichloromethane (40 mL) at 0° C. The reaction was aloud to reach room temperature and stirred for 6 h. The reaction was quenched by addition of saturated aqueous sodiumhydrogen carbonate and extracted with dichloromethane. The organic phase was washed with brine, dried over magnesium sulfate and evaporated. Purification by flash chromatography using ethyl acetate afforded 0.302 g (51% yield) of the title compound. 1H NMR (DMSO-d6) δ 7.86-7.77 (m, 2 H), 7.53-7.46 (m, 2 H), 7.37 (s, 2 H), 7.07 (t, J=7.83 Hz, 1 H), 6.96 (br s, 2 H), 6.72-6.58 (m, 3 H); MS (API) m/z 370 [M+1]+.

Workup

  1. customto reach room temperature
  2. customThe reaction was quenched by addition of saturated aqueous sodiumhydrogen carbonate
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2415511a668c4b77ad08c24654609315
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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