Water → HCID 57932955, compound

HRID 1432687Notes

Reaction equation

HRID 1432687 reaction equation
Br[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(Cl)Cl.O>COCCOC.O.CCO.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>[CH2:17]([CH:16]([C:15]1[C:10]2[N:11]([C:7]([C:6]3[S:5][C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:3][C:2]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:8]([CH3:22])[N:9]=2)[N:12]=[C:13]([CH3:21])[CH:14]=1)[CH2:19][CH3:20])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 57933083HCID 57933083, compound

Product 1

HCID 57932955HCID 57932955, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
160 °C

Procedure

50 mg of 3-(4-Bromo-2-morpholin-4-yl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.11 mmol), 40 mg of phenylboronic acid (0.33 mmol) and 0.27 ml of 2 M Na2CO3aq. (0.55 mmol) are put in 2.5 ml of DME/water/EtOH=7/3/1. N2 gas is bubbled in the mixture for 20 min and 20 mg of Pd(PPh3)4 (0.017 mmol) is added. The vial is sealed and heated at 160° C. for 30 min in Microwave. The reaction mixture are added CH2Cl2 and water and the organic layer is separated, washed with brine, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=10:1) to give 27 mg of the title compound. Yield 54% mass spectrum (m/e): 462 (M+1). δ 8.29 (m, 1H), 7.60 (m, 2H), 7.44 (m, 1H), 7.22 (m, 1H), 6.70 (s, 1H), 3.90 (t, J=4.6 Hz, 4H), 3.64 (t, J=5.0 Hz, 4H), 3.36 (m, 1H), 2.52 (s, 3H), 2.09 (s, 3H), 1.86 (m, 4H), 0.90 (t, J=7.4 Hz, 6H).

Workup

  1. customN2 gas is bubbled in the mixture for 20 min
  2. customThe vial is sealed
  3. customthe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-2945fd837d02449284c05953ff16965c
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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