Sodium Carbonate → HCID 118524120, compound

HRID 531454Notes

Reaction equation

HRID 531454 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[N:28]1[CH:32]=[CH:31][C:30](B(O)O)=[N:29]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:30]3[CH:31]=[CH:32][N:28]([CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27][O:22]4)[N:29]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 55253760[1-(Oxan-2-yl)-1H-pyrazol-3-yl]boronic acid

Product 1

HCID 118524120HCID 118524120, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

Using the same reaction conditions as described in step-i of example 1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 1) (100 mg, 0.209 mmol) was coupled with (1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)boronic acid (103 mg, 0.524 mmol) using sodium carbonate (66 mg, 0.627 mmol) and Pd(PPh3)2Cl2 (7 mg, 0.0104 mmol) in DME/water (3/0.7 ml) to afford 60 mg (crude) product. MS: m/z=501.1 (M+1).

Workup

  1. customthe same reaction conditions
  2. customto afford 60 mg (crude) product

Sources & evidence

ORD record
ord-2800c7cfa23b4fb4bfb2320b68ccfc7d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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