Ethyl Acetate → HCID 86702540, compound

HRID 877067Notes

Reaction equation

HRID 877067 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][CH:25]=[C:24]5Br)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[CH3:45][N:46](C)C(=O)C>[Zn].[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][CH:25]=[C:24]5[C:45]#[N:46])=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 31374DimethylacetamideHCID 86702541HCID 86702541, compound

Product 1

HCID 86702540HCID 86702540, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 23994ZincCatalyst2×

Conditions

Temperature
110 °C

Procedure

150 mg (0.26 mmol) {1-[4-(7-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester (intermediate example Int-2-1), 1.7 mg (0.026 mmol) zinc, 21.6 mg (0.026 mmol) bis(diphenylphosphino)ferrocenedichloropalladium(II) and 61.8 mg (0.53 mmol) zinc cyanide in 2.2 mL N,N-dimethylacetamide, (degassed) were stirred in the microwave for four hours at 110° C. After addition of a further equivalent of zinc cyanide and a spatelspitze of zinc and bis(diphenylphosphino)ferrocenedichloropalladium(II) stirring was continued for three hours at 110° C. Despite an incomplete reaction the mixture was worked up. After addition of ethyl acetate the organic phase was washed twice with water and saturated ammonium chloride, dried over sodium sulfate, filtrated, and the solvent was removed. 274 mg {1-[4-(7-Cyano-3-phenylpyrimido[1,2-b]indazol-2-yl)-phenyl]cyclobutyl}carbamic acid tert-butylester were obtained which were used without purification in the next step (cleavage of the protecting group).

Workup

  1. customDespite an incomplete reaction the mixture
  2. washwas washed twice with water and saturated ammonium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-a18abe61d81e47e4b2ee75395d938d2d
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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