Sodium Carbonate → HCID 86702534, compound

HRID 877058Notes

Reaction equation

HRID 877058 reaction equation
C(C1C=C([C:9]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][N:12]3[N:13]=[C:14]4[C:19]([CH:18]=[CH:17][C:16]([C:20]5[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=5)[C:23]#[N:24])=[CH:15]4)=[C:11]3[N:10]=2)C=CC=1)#N.[C:36]([O:40][C:41](=[O:62])[NH:42][C:43]1([C:47]2[CH:52]=[CH:51][C:50](B3OC(C)(C)C(C)(C)O3)=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44]1)([CH3:39])([CH3:38])[CH3:37].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[C:36]([O:40][C:41](=[O:62])[NH:42][C:43]1([C:47]2[CH:48]=[CH:49][C:50]([C:9]3[C:29]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:28][N:12]4[N:13]=[C:14]5[C:19]([CH:18]=[CH:17][C:16]([C:20]6[CH:27]=[CH:26][CH:25]=[C:22]([C:23]#[N:24])[CH:21]=6)=[CH:15]5)=[C:11]4[N:10]=3)=[CH:51][CH:52]=2)[CH2:44][CH2:45][CH2:46]1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamateHCID 67973853HCID 67973853, compound

Product 1

HCID 86702534HCID 86702534, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

179 mg of the mixture described in step 1,3-(2-chloro-3-phenylpyrimido[1,2-b]indazol-8-yl)benzonitrile and the byproduct 3-[2-(3-cyanophenyl)-3-phenyl-pyrimido[1,2-b]indazol-8-yl]benzonitrile, 210.5 mg (0.56 mmol) {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamic acid tert-butyl ester, 38.4 mg (0.047 mmol) bis(diphenylphosphino)ferrocenedichloropalladium(II) and 0.87 mL aqueous sodium carbonate solution (10%) in 1.6 mL dimethoxyethane were heated in the microwave oven for 60′ at 120° C. After the usual work up described in step 1, the mixture (239.4 mg) was used in the next step without further purification.

Workup

  1. customthe mixture (239.4 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-a2fe71ab674d4b8ea5d8841c9e1c3f85
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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