Sodium Carbonate → HCID 57786651, compound

HRID 1969116Notes

Reaction equation

HRID 1969116 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12]([NH:14][CH3:15])=[O:13])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[OH:16][C:17]([C:20]1[CH:44]=[CH:43][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29](B3OC(C)(C)C(C)(C)O3)[C:28]=2[CH3:42])=[O:25])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>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(COC)OC>[OH:16][C:17]([C:20]1[CH:44]=[CH:43][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:2]3[CH:3]=[C:4]([NH:11][C:12]([NH:14][CH3:15])=[O:13])[C:5]4[N:6]([CH:8]=[CH:9][N:10]=4)[CH:7]=3)[C:28]=2[CH3:42])=[O:25])=[CH:22][CH:21]=1)([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 57662782HCID 57662782, compoundHCID 57786794HCID 57786794, compound

Product 1

HCID 57786651HCID 57786651, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A 5 mL Microwave Reactor Vessel was charged with 1-(6-Bromo-imidazo[1,2-a]pyridin-8-yl)-3-methyl-urea (85 mg, 0.317 mmol), 4-(1-Hydroxy-1-methyl-ethyl)-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (125 mg, 1 eq), tetrakis(triphenylphosphine)palladium (37 mg, 0.1 eq), 1M sodium carbonate (1 mL) and dimethoxyethane (2 mL). The reaction mixture was irradiated for 10 minutes at 150° C. on the Microwave Reactor. The reaction mixture was then partitioned between ethyl acetate (150 mL) and water (50 ml). Separated the layers and washed the organic layer with water (4×50 mL), then finally washed with brine (1×50 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by Preparative Thin Layer Chromatography, eluting with 50% acetone in hexanes to give 4-(1-Hydroxy-1-methyl-ethyl)-N-{2-methyl-3-[8-(3-methyl-ureido)-imidazo[1,2-a]pyridin-6-yl]-phenyl}-benzamide as an off-white powder (20 mg), ((M+H)+=458).

Workup

  1. customThe reaction mixture was irradiated for 10 minutes at 150° C. on the Microwave Reactor
  2. customThe reaction mixture was then partitioned between ethyl acetate (150 mL) and water (50 ml)
  3. customSeparated the layers
  4. washwashed the organic layer with water (4×50 mL)
  5. washfinally washed with brine (1×50 mL)
  6. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by Preparative Thin Layer Chromatography
  10. washeluting with 50% acetone in hexanes

Sources & evidence

ORD record
ord-cb1e1b21712f4abf867b919b68307d65
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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