Sodium Carbonate → HCID 86619584, compound

HRID 2236659Notes

Reaction equation

HRID 2236659 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH2:6]/[C:5]/2=[CH:12]\[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[C:17]([OH:25])[CH:16]=1.[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[OH:25][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH2:22][CH2:23][CH3:24])[CH2:14][NH:13]/[CH:12]=[C:5]1\[CH2:6][N:7]=[CH:8][C:9]2[C:4]\1=[CH:3][C:2]([C:28]1[CH:29]=[CH:30][S:26][CH:27]=1)=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 86619585HCID 86619585, compound

Product 1

HCID 86619584HCID 86619584, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

An amount of (4Z)-6-bromo-4-{[(3-hydroxy-4-propoxybenzyl)amino]methylene}isoquinoline}-1,3(2H,4H)-dione (135.0 mg, 0.32 mmol) is dissolved in 80% mixture of N,N dimethylformamide/water (4 mL). Tetrakistriphenylphosphine (44.0 mg, 0.04 mmol) is added followed by 3-thiopheneboronic acid (48.4 mg, 0.38 mmol) along with sodium carbonate (67.8 mg, 0.64 mmol). The reaction mixture is heated to 150° C.-180° C. for 3 minutes under microwave irradiation. The solvent is concentrated and the reaction mixture is partitioned between ethyl acetate (50 ml) and water (50 ml). The crude solid is then purified by high performance liquid chromatography to give 25.0 mg of a white solid. MS (ESI) m/z 549.8 (M+1).

Workup

  1. temperatureThe reaction mixture is heated to 150° C.-180° C. for 3 minutes under microwave irradiation
  2. concentrationThe solvent is concentrated
  3. customthe reaction mixture is partitioned between ethyl acetate (50 ml) and water (50 ml)
  4. customThe crude solid is then purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-bab779256899465290282e8c5c0f49c3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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