Acetonitrile → HCID 58205036, compound

HRID 2044522Notes

Reaction equation

HRID 2044522 reaction equation
I[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:19]=1.[CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)([CH3:22])[CH3:21].C(#N)C>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>[CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:19]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 27734772-Isopropylbenzeneboronic acidHCID 58204516Methyl 2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxylate

Product 1

HCID 58205036HCID 58205036, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolvent

Procedure

Methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (80 mg, 1 eq), 2-isopropylphenylboronic acid (65 mg, 1.75 eq), and tetrakis(triphenylphosphine)palladium (10 mg, 0.05 eq), in 1.0 M aqueous sodium carbonate (1.0 mL) and acetonitrile (1.0 mL) were heated to 140° C. for 10 min in a sealed microwave reactor. The crude reaction mixture was concentrated and purified using reverse phase HPLC to yield 298 (23 mg). ESI-MS: 363.1(M)+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. custompurified

Sources & evidence

ORD record
ord-3e58c0b9a125470ba62ef33805a5ada1
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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