Triethylamine → HCID 178504185, compound

HRID 632889Notes

Reaction equation

HRID 632889 reaction equation
Br[C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:11][Si:12]([CH3:16])([CH3:15])[C:13]#[CH:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][Si:12]([C:13]#[C:14][C:3]1[CH:4]=[C:5]2[N:10]=[CH:9][NH:8][C:6]2=[N:7][CH:2]=1)([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 178419319HCID 178419319, compound

Product 1

HCID 178504185HCID 178504185, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 1.2 g (6.1 mmol) 5-bromo-3H-imidazol[4,5-b]pyridine and 1.2 mL (8.4 mmol) 1-trimethylsilyl-ethyne using 34 mg (0.18 mmol) CuI, 159 mg (0.61 mmol) triphenylphosphine, 128 mg (0.18 mmol) PdCl2(PPh3)2 and 10.1 mL (72.7 mmol) triethylamine in 10 mL dry THF. The formed precipitate is filtered off and the product is purified by RP-HPLC using an ACN/H2O gradient. Yield: 606 mg (46%).

Workup

  1. filtrationThe formed precipitate is filtered off
  2. customthe product is purified by RP-HPLC

Sources & evidence

ORD record
ord-ad7d44b07c8a4a0299c049f35f559563
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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