3-Bromopyridine → HCID 10546110, compound

HRID 724949Notes

Reaction equation

HRID 724949 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:14]#[CH:15])=[CH:13][C:8]=2[C:7](=[O:16])[N:6]([CH3:17])[C:5]2[CH:18]=[CH:19][CH:20]=[N:21][C:4]1=2)[CH3:2].Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:14]#[C:15][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][C:8]=2[C:7](=[O:16])[N:6]([CH3:17])[C:5]2[CH:18]=[CH:19][CH:20]=[N:21][C:4]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 122863-BromopyridineHCID 10802535HCID 10802535, compound

Product 1

HCID 10546110HCID 10546110, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
85 °C

Procedure

A mixture containing 5,11-dihydro-11-ethyl-8-ethynyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.19 g, 0.68 mmol), 3-bromopyridine (0.07 mL, 0.73 mmol), tetrakis(triphenylphosphine)palladium(0), triethylamine (2 mL), and 1 crystal of BHT was heated at 85° C. in a sealed tube for 7 hours. Solvent was removed, and the residue was purified by flash chromatography, eluting with ethyl acetate/hexanes, and recrystallization from ethanol/hexanes to give 0.16 g of the title compound as yellow crystals, m.p. 178°-180° C.

Workup

  1. customSolvent was removed
  2. customthe residue was purified by flash chromatography
  3. washeluting with ethyl acetate/hexanes, and recrystallization from ethanol/hexanes

Sources & evidence

ORD record
ord-52645f3a74514efe9247612b54d37478
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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