Sodium Carbonate → HCID 86702539, compound

HRID 877064Notes

Reaction equation

HRID 877064 reaction equation
Cl[C:2]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][N:5]2[N:6]=[C:7]3[C:12]([C:11]([C:13]4[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=4)=[CH:10][CH:9]=[CH:8]3)=[C:4]2[N:3]=1.[C:29]([O:33][C:34](=[O:55])[NH:35][C:36]1([C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][CH:41]=2)[CH2:39][CH2:38][CH2:37]1)([CH3:32])([CH3:31])[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.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>[C:29]([O:33][C:34](=[O:55])[NH:35][C:36]1([C:40]2[CH:41]=[CH:42][C:43]([C:2]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][N:5]4[N:6]=[C:7]5[C:12]([C:11]([C:13]6[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=6)=[CH:10][CH:9]=[CH:8]5)=[C:4]4[N:3]=3)=[CH:44][CH:45]=2)[CH2:37][CH2:38][CH2:39]1)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 58326444tert-Butyl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutyl)carbamateHCID 86702537HCID 86702537, compound

Product 1

HCID 86702539HCID 86702539, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

114 mg (0.3 mmol) 4-(2-Chloro-3-phenylpyrimido[1,2-b]indazol-10-yl)benzonitrile, 122.9 g (0.3 mmol) {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester, 34.6 mg (0.03 mmol) tetrakistriphenylphosphinepalladium(0) and 95 mg (0.90 mmol) sodium carbonate in 3.2 mL dioxane and 0.45 mL water were heated in a microwave vial which had been sealed with a microwave cap over night at 105° C. (heating block). After the usual work up, the crude mixture (235 mg) was used in the next step without further purification.

Workup

  1. customhad been sealed with a microwave
  2. customcap over night at 105° C.
  3. temperature(heating block)
  4. customAfter the usual work up, the crude mixture (235 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-e2a68fa46ee548e58a8a17feff8a7a47
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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