1,4-Dioxane → [6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-(1H-indazol-5-yl)-amine

HRID 746456Notes

Reaction equation

HRID 746456 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[CH:15]3)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:34][CH2:33]OCC1>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.O>[NH2:11][C:12]1[CH:20]=[C:19]([C:2]2[N:3]=[C:4]([NH:11][C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[CH:15]4)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=2)[CH:18]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 57447601(6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indazol-5-yl)-amine

Product 1

HCID 57447602[6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-(1H-indazol-5-yl)-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 1.00 eq. of (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indazol-5-yl)-amine, 1.1 eq. of R4-substituted boronic acid, and 0.10 eq. of Pd(PPh3)4, 2.2 eq. of K3PO4 in 4:1 1,4-dioxane:water is heated to 90° C. for 24 hr. The mixture is cooled to RT and partitioned between EtOAc and sat. NaHCO3. The aqueous phase is extracted with EtOAc and combined extracts are dried over Na2SO4. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (EtOAc) to yield (5).

Workup

  1. custompartitioned between EtOAc and sat. NaHCO3
  2. extractionThe aqueous phase is extracted with EtOAc and combined extracts
  3. dry with materialare dried over Na2SO4
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting residue is purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-0b2c6ba0e4db41a1bc5964934ff7a55d
Source dataset
uspto-grants-2008_07
Patent number
US07393848B2

Reaction notes

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