Sodium Carbonate → HCID 67979477, compound

HRID 528769Notes

Reaction equation

HRID 528769 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:22][CH2:21][C:12]2=[C:13](Cl)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.B1([C:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH:39]=2)OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[C:1]([O:5][C:6]([N:8]1[CH2:22][CH2:21][C:12]2=[C:13]([C:38]3[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH:39]=3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 4692812210-Chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

Product 1

HCID 67979477HCID 67979477, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Procedure

To 0.075 g (0.23 mmol) 10-chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester in a microwave tube were added 3 mL dioxane, 1 mL MeOH, 79 mg (0.25 mmol) (N-tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 0.6 mL aqueous Na2CO3 (2 M), 19 mg (0.023 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium (II) under nitrogen and the reaction was subjected to microwave irradiation (discoverer, 100° C., 250 Watts) for 15 minutes. After evaporation of the solvent the product was purified by column chromatography (silica, DCM/MeOH 100:2).

Workup

  1. customthe reaction was subjected to microwave irradiation (discoverer, 100° C., 250 Watts) for 15 minutes
  2. customAfter evaporation of the solvent the product
  3. customwas purified by column chromatography (silica, DCM/MeOH 100:2)

Sources & evidence

ORD record
ord-7dad8cd9a8b34e3082d4d13727491eb2
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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