Sodium Carbonate → HCID 58529618, compound

HRID 1972804Notes

Reaction equation

HRID 1972804 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[N:24]3[C:19]([C:20]([NH2:25])=[N:21][CH:22]=[N:23]3)=[C:18](Br)[CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([N:34]1[CH:42]=[C:41]2[C:36]([CH:37]=[C:38](B3OC(C)(C)C(C)(C)O3)[CH:39]=[CH:40]2)=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[N:24]3[C:19]([C:20]([NH2:25])=[N:21][CH:22]=[N:23]3)=[C:18]([C:38]3[CH:39]=[CH:40][C:41]4[C:36]([CH:37]=3)=[N:35][N:34]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:42]=4)[CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 58529384HCID 58529384, compound

Product 1

HCID 58529618HCID 58529618, compound

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Conditions

Temperature
80 °C

Procedure

The product from step 3 (330 mg, 0.78 mmol) and Intermediate C (337 mg, 1.01 mmol), were dissolved in 7 mL dioxane:ethanol (5:2) and the mixture was treated with 2 M sodium carbonate (7 mL) and 1,1′-bis(diphenylphosphinoferrocenyl)palladium dichloride (27 mg) was added. The mixture was heated to 80° C. with stirring for 4 h. The mixture was allowed to cool and filtered through Celite®. Ethyl acetate was added and the product was extracted from the aqueous solution. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue purified by Biotage® to provide the title compound. 1H NMR (CD2Cl2) δ 1.50 (s, 9H), 1.60-2.00 (m, 3H), 2.80 (m, 2H), 3.80 (t, 1H), 4.10 (m, 3H), 5.60 (s, 2H), 7.20 (d, 1H), 7.40 (m, 6H), 7.80 (dd, 2H), 8.10 (m, 2H). LC-MS [M+H]+=574.1, RT=3.36 min.

Workup

  1. additionwas added
  2. temperatureto cool
  3. filtrationfiltered through Celite®
  4. additionEthyl acetate was added
  5. extractionthe product was extracted from the aqueous solution
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue purified by Biotage®

Sources & evidence

ORD record
ord-6141d0fb1cd14a9d9e2a055c44f7ca4c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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