Sodium t-butoxide → 4-[5-(2-Ethoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl benzamide

HRID 1924902Notes

Reaction equation

HRID 1924902 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][N:5]=1)[CH3:2].Br[C:20]1[N:25]2[CH:26]=[CH:27][N:28]=[C:24]2[C:23]([NH:29][C:30]2[CH:45]=[CH:44][C:33]([C:34]([NH:36][CH2:37][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)=[O:35])=[CH:32][CH:31]=2)=[N:22][CH:21]=1.CC([O-])(C)C.[Na+]>CN(C=O)C.O.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>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:20]2[N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[C:23]([NH:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([NH:36][CH2:37][C:38]4[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=4)=[O:35])=[CH:44][CH:45]=3)=[N:22][CH:21]=2)[CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 457860072-Ethoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 866167454-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl benzamide

Product 1

HCID 866167464-[5-(2-Ethoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl benzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-ethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (85 mg, 0.34 mmol), 4-(5-bromoimidazo[1,2-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl benzamide (150 mg, 0.35 mmol), Pd(PPh3)4 (33 mg, 0.028 mmol) and NaOtBu (109 mg, 1.1 mmol) in DMF:water (3:1, 9 mL) is heated at 85° C. for 18 hours. After this time the reaction mixture is cooled to room temperature and the solvents removed in vacuo. The residue is chromatographed on silica gel, eluting with DCM followed by 95:5 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated to afford the title ethoxypyridine as a solid.

Workup

  1. temperatureAfter this time the reaction mixture is cooled to room temperature
  2. customthe solvents removed in vacuo
  3. customThe residue is chromatographed on silica gel
  4. washeluting with DCM
  5. additionNH3 (7M in MeOH), and the fractions containing the desired product
  6. customevaporated

Sources & evidence

ORD record
ord-eb3ad01dfebc4c9ab6c0f1c1ae62db24
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

Loading…