Ethyl Acetate → {1-[4-(9-Fluoro-4-cyclopropylamino-3-phenyl-pyrimido[1,2-b]indazol-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester

HRID 877054Notes

Reaction equation

HRID 877054 reaction equation
Cl[C:2]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([NH:22][CH:23]2[CH2:25][CH2:24]2)[N:5]2[N:6]=[C:7]3[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[C:26]([O:30][C:31](=[O:52])[NH:32][C:33]1([C:37]2[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][CH:38]=2)[CH2:36][CH2:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(COC)OC.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:26]([O:30][C:31](=[O:52])[NH:32][C:33]1([C:37]2[CH:38]=[CH:39][C:40]([C:2]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:14]([NH:22][CH:23]4[CH2:25][CH2:24]4)[N:5]4[N:6]=[C:7]5[C:12]([CH:11]=[C:10]([F:13])[CH:9]=[CH:8]5)=[C:4]4[N:3]=3)=[CH:41][CH:42]=2)[CH2:34][CH2:35][CH2:36]1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamateHCID 86702530(2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazol-4-yl)cyclopropylamine

Product 1

HCID 86702531{1-[4-(9-Fluoro-4-cyclopropylamino-3-phenyl-pyrimido[1,2-b]indazol-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

300 mg (0.9 mmol) (2-Chloro-9-fluoro-3-phenylpyrimido[1,2-b]indazol-4-yl)-cyclopropylamine, 444.4 mg (1.2 mmol) {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester, 1.6 mL aqueous sodium carbonate (10%) and 31.2 mg (0.04 mmol) 1,1 bis(diphenylphosphino)ferrocenedichloropalladium(II) were given in 2.9 mL dimethoxyethane and heated for 40′ in the microwave at 120° C. The reaction mixture was poured on water and ethyl acetate and stirred vigorously for 30 minutes. The organic phase was separated and washed twice with brine. After drying with sodium sulfate the solvent was removed and the crude residue (720 mg) was used in the next step without further purification.

Workup

  1. customThe organic phase was separated
  2. washwashed twice with brine
  3. dry with materialAfter drying with sodium sulfate the solvent
  4. customwas removed
  5. customthe crude residue (720 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-301e7794ec2f4164952ae683171e6a4a
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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