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Triethylamine → HCID 66705970, compound

HRID 1529198
Notes
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Reaction equation

HRID 1529198 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH3:10])=[N:6][CH:7]=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.C(OCC)(=O)C.C1CCCCC1.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>[CH2:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([C:14]#[C:13][Si:12]([CH3:16])([CH3:15])[CH3:11])=[CH:7][N:6]=1)[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 225049165-Bromo-N-ethylpyridin-2-amine

Product 1

HCID 66705970HCID 66705970, compound

Reagents, catalysts & solvents 4

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8078CyclohexaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

The title compound is synthesized according to general procedure GP2 starting from 909 mg (4.5 mmol) 5-bromo-2-ethylamino-pyridine and 0.89 mL (6.3 mmol) 1-trimethylsilyl-ethyne using 26 mg (0.13 mmol) CuI, 118 mg (0.45 mmol) triphenylphosphine, 82 mg (0.12 mmol) PdCl2(PPh3)2 and 6.3 mL (45.0 mmol) triethylamine in 7 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient.

Workup

  1. extractionthe organic phase is extracted with water and brine
  2. customThe product is purified by chromatography on silica gel using a hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-3da854f52bc14baebc29269aa6fa345a
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090564B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes