4-Fluorophenylboronic acid → HCID 11151773, compound

HRID 1297325Notes

Reaction equation

HRID 1297325 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:5]([NH:8][CH:9]=O)=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])(O)=O.[Na+]>COCCOC.O.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>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:3]=[C:4]3[N:11]([CH2:12][C:13]4[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=4)[CH:9]=[N:8][C:5]3=[N:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 58914552N-(5-Bromo-3-{[(4-methoxyphenyl)methyl]amino}pyrazin-2-yl)formamide

Product 1

HCID 11151773HCID 11151773, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of N-[5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-formamide (160 mg, 0.47 mmol), 4-fluoro-phenyl boronic acid (200 mg, 1.44 mmol), Pd(PPh3)2Cl2 (2 mg, 0.0028 mmol), and NaHCO3 (118 mg, 1.41 mmol) in DME (1 mL) and water (0.2 mL) was put in a microwave reaction tube and reacted in a microwave reactor at 110° C. for 7 minutes. The reaction mixture was partitioned in ethyl acetate and water, and the organic layer was evaporated. The residue was purified on a C-18 reversed phase preparative HPLC eluting with Methanol/Acetontrile containing 0.1% trifluoroacetic acid to provide 6-(4-fluoro-phenyl)-1-(4-methoxy-benzyl)-1H-imidazo[4,5-b]pyrazine as a white solid (48 mg).

Workup

  1. customwas put in a microwave reaction tube
  2. customreacted in a microwave reactor at 110° C. for 7 minutes
  3. customThe reaction mixture was partitioned in ethyl acetate
  4. customwater, and the organic layer was evaporated
  5. customThe residue was purified on a C-18
  6. washeluting with Methanol/Acetontrile
  7. additioncontaining 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-58a53ad45dcc41739a867e8ef5931eee
Source dataset
uspto-grants-2007_07
Patent number
US07250417B2

Reaction notes

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