Triethylamine → HCID 58516265, compound

HRID 1919181Notes

Reaction equation

HRID 1919181 reaction equation
I[C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:4][CH:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([B:27]([OH:29])[OH:28])=[CH:23][CH:22]=1)#[CH:20].C(N(CC)CC)C>CN(C=O)C.[Cu]I.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:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:5]1[NH:6][C:2]([C:20]#[C:19][C:21]2[CH:22]=[CH:23][C:24]([B:27]([OH:29])[OH:28])=[CH:25][CH:26]=2)=[CH:3][N:4]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 23436919(4-Ethynylphenyl)boronic acidHCID 58498756(S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 58516265HCID 58516265, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Nitrogen was bubbled through a solution of (S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (150 mg, 0.41 mmol), 4-ethynylphenylboronic acid (90 mg, 0.62 mmol) and copper(I) iodide (15.7 mg, 0.083 mmol) in DMF (5 mL) and triethylamine (0.30 mL, 2.0 mmol) for 15 min. Then Pd(PPh3)4 (23.86 mg, 0.021 mmol) was added and the reaction mixture was vacuum flushed with nitrogen (4×,), sealed and heated at 60° C. ON. The crude reaction was concentrated to dryness, dissolved into DMF/MeOH and purified by Prep HPLC (MeOH/water with ammonium acetate buffer) to yield (S)-4-((2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)ethynyl)phenylboronic acid (113.8 mg, 0.299 mmol) as a light yellow solid.

Workup

  1. customflushed with nitrogen (4×,)
  2. customsealed
  3. customThe crude reaction
  4. concentrationwas concentrated to dryness
  5. dissolutiondissolved into DMF/MeOH
  6. custompurified by Prep HPLC (MeOH/water with ammonium acetate buffer)

Sources & evidence

ORD record
ord-b805775a0c66431b85070c61ab855b25
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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