Potassium Carbonate → HCID 86705363, compound

HRID 1773659Notes

Reaction equation

HRID 1773659 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[N:6]([C:8](I)=[CH:9][N:10]=2)[N:7]=1.CCN(C(C)C)C(C)C.[N:22]1([CH2:28][CH2:29][NH2:30])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH3:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[C:38](=[O:41])[NH:39][CH3:40].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.C1COCC1.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].C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:30][CH2:29][CH2:28][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:6]([C:8]([C:34]3[CH:35]=[CH:36][C:37]([C:38]([NH:39][CH3:40])=[O:41])=[C:32]([CH3:31])[CH:33]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 66691681HCID 66691681, compoundHCID 86705359HCID 86705359, compound

Product 1

HCID 86705363HCID 86705363, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2.01 g (5 mmol) 6,8-dibromo-3-iodoimidazo[1,2-b]pyridazine which was prepared according to intermediate example 96c in NMP (15 mL) were added 1.94 g (15 mmol) DIPEA and 1.30 g (10 mmol) 2-(morpholin-4-yl)ethanamine in one portion at rt. After heating for 2 h at 70° C., 100 mL DCM were added and the mixture was washed with water (3×100 mL). The organic phase was dried over sodium sulphate and evaporated to yield a brownish solid which was used without further purification in the next step. To a stirred solution of the remaining solid in 20 mL THF were added 1.16 g (6 mmol) [3-methyl-4-(methylcarbamoyl)phenyl]boronic acid which was prepared according to intermediate example 562b, 15 mL aqueous potassium carbonate solution (15 mmol, 1M), 816 mg Pd(dppf)Cl2 (1 mmol) and the mixture was heated for 41 h at 70° C., to yield after working up and purification 2.35 g (99%) of the title compound.

Workup

  1. washthe mixture was washed with water (3×100 mL)
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated
  4. customto yield a brownish solid which
  5. customwas used without further purification in the next step
  6. customwas prepared
  7. temperaturethe mixture was heated for 41 h at 70° C.
  8. customto yield
  9. custompurification 2.35 g (99%) of the title compound

Sources & evidence

ORD record
ord-e43fa7be1a60476cb17dc9d3c50c88fe
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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