Cesium carbonate → HCID 46192921, compound

HRID 1943861Notes

Reaction equation

HRID 1943861 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[C:19](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH2:20].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([NH:20][C:19](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=[C:4]2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67078557HCID 67078557, compound

Product 1

HCID 46192921HCID 46192921, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pd2(dibenzylidene acetone)3 (“Pd2dba3”; 0.031 g, 0.033 mmol) was added to a suspension of 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.110 g, 0.335 mmol), tert-butyl carbamate (0.118 g, 1.00 mmol), Xantphos (0.039 g, 0.067 mmol), Cs2CO3 (0.163 g, 0.503 mmol) in THF (10 mL). The reaction mixture was purged with argon for 10 minutes and heated to reflux under argon overnight. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (9:1) to give tert-butyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (0.100 g, 82%) as an oil.

Workup

  1. customThe reaction mixture was purged with argon for 10 minutes
  2. temperatureheated
  3. temperatureto reflux under argon overnight
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-736f956cbc0b4bf2bf1fa4c94c7ef7c5
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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