9-Chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine → 12-Chloro-4-(pyridin-2-yl)-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

HRID 1530498Notes

Reaction equation

HRID 1530498 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10](I)[N:11]=1)[CH2:7][CH2:6][O:5]2.[Br-].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Zn+]>C1COCC1.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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2

Participants

5

Reactant 2

HCID 582047809-Chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepineHCID 178418723HCID 178418723, compound

Product 1

HCID 8667145812-Chloro-4-(pyridin-2-yl)-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaeneYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 12-chloro-4-iodo-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (1.00 g, 2.88 mmol), pyridin-2-ylzinc(II) bromide (0.5 M THF) (8.60 mL), Pd(PPh3)4 (498 mg, 0.432 mmol) in THF (30 mL) was stirred at 35° C. for 16 hr. After removal of the solvent, the residue was washed with acetone to afford 12-chloro-4-(pyridin-2-yl)-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (750 mg, 87% yield) as yellow solid. LCMS (ESI) m/z: 299.0 [M+H+].

Workup

  1. customAfter removal of the solvent
  2. washthe residue was washed with acetone

Sources & evidence

ORD record
ord-c85b8aa636454e7cabba237e07ed6f45
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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