Boron tribromide → HCID 59436013, compound

HRID 1802498Notes

Reaction equation

HRID 1802498 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][C:15]1[C:24]2[CH:25]=[CH:26][N:27]=[C:28]([O:29]C)[C:23]=2[C:22]2[C:17](=[CH:18][CH:19]=[N:20][CH:21]=2)[N:16]=1.ClC1C=C(SC(F)(F)F)C=C(Cl)C=1NC1C2C=CN=C(OCC)C=2C2C(=CC=NC=2)N=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[Cl:13][C:4]1[CH:5]=[C:6]([S:8][C:9]([F:10])([F:11])[F:12])[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:14][C:15]1[C:24]2[CH:25]=[CH:26][NH:27][C:28](=[O:29])[C:23]=2[C:22]2[C:17](=[CH:18][CH:19]=[N:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 59435968HCID 59435968, compoundHCID 59436077HCID 59436077, compound

Product 1

HCID 59436013HCID 59436013, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

A solution of N-{2,6-dichloro-4-[(trifluoromethyl)thio]phenyl}-10-methoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (15 mg, 0.03 mmol), N-{2,6-dichloro-4-[(trifluoromethyl)thio]phenyl}-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (15 mg, 0.03 mmol) and boron tribromide (0.256 ml, 0.26 mmol) in chloroform (10 ml) was stirred in a microwave vial. The vial was sealed and heated to 85° C. for 45 minutes. The crude reaction mixture was washed with sodium bicarbonate and extracted with 3:1 chloroform:isopropanol. Combined organics were concentrated under reduced pressure to afford the title compound.

Workup

  1. customThe vial was sealed
  2. customThe crude reaction mixture
  3. washwas washed with sodium bicarbonate
  4. extractionextracted with 3:1 chloroform
  5. concentrationCombined organics were concentrated under reduced pressure

Sources & evidence

ORD record
ord-469d2778f4b14cc1ad8092e3adb7a7bd
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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