Sodium Carbonate → HCID 59198493, compound

HRID 1896536Notes

Reaction equation

HRID 1896536 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[N:10][CH:11]=[C:12]([C:15]#[N:16])[C:13]=3[S:14][C:4]=2[CH:3]=1.B1([C:33]2[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=2)OCCCO1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:9]2[C:8]3[C:5]4[CH:6]=[CH:7][C:2]([C:33]5[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=5)=[CH:3][C:4]=4[S:14][C:13]=3[C:12]([C:15]#[N:16])=[CH:11][N:10]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 591984657-Bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile

Product 1

HCID 59198493HCID 59198493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 7-bromo-1-[(4-methoxybenzyl)amino][1]benzothieno[3,2-c]pyridine-4-carbonitrile (Example 12, Step 9) in DMF (0.1 M) were added the pyridine-3-boronic acid 1,3-propanediol cyclic ester (1.5 equiv), 2 M Na2CO3 (3 equiv) and PdCl2dppf (0.05 equiv). The mixture was heated in the microwave reactor at 110° C. for 10 min. The reaction mixture was partitioned between EtOAc and saturated NaHCO3. The organic phase was separated, dried over MgSO4, filtered, evaporated and purified by flash chromatography (70:30 hexanes/EtOAc to 100% EtOAc) to provide the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated NaHCO3
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography (70:30 hexanes/EtOAc to 100% EtOAc)

Sources & evidence

ORD record
ord-99b5f753f053439b8c1b9ab0d5938148
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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