Sodium Carbonate → HCID 87867171, compound

HRID 1360348Notes

Reaction equation

HRID 1360348 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[CH:3]=1.[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[O:28][C:27]=2[C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC>[CH:23]1[C:31]2[C:30]3[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=3[O:28][C:27]=2[C:26]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=3)[CH:3]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 59818073HCID 59818073, compound2×

Product 1

HCID 87867171HCID 87867171, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

tert-Butyl N-[4-(6-chloropyrimidin-4-ylamino)-phenyl]carbamate (compound C1) (10.1 g, 31 mmol) and 4-dibenzofurane boronic acid (9.96 g, 47 mmol) are heated in dimethoxyethane (500 mL) under an inert atmosphere with dichloro-bis(tricyclohexylphosphine)-palladium(II) (2.28 g, 3.1 mmol) and an aqueous Na2CO3-solution (32.8 g in 310 mL of water) for 4 h at 80° C. After evaporation and extraction of the residue, the product is purified by crystallization.

Workup

  1. customAfter evaporation and extraction of the residue
  2. customthe product is purified by crystallization

Sources & evidence

ORD record
ord-bacdb1f649d341dcaf48d227abac94ab
Source dataset
uspto-grants-2011_02
Patent number
US07879853B2

Reaction notes

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