1,2-Dimethoxyethane → HCID 58979590, compound

HRID 1180567Notes

Reaction equation

HRID 1180567 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13](Br)[CH:14]=[N:15][CH:16]=2)[N:11]=1)=[O:9].OB(O)[C:23]1[S:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>CO.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([C:23]3[S:27][C:26]([C:28]([OH:30])=[O:29])=[CH:25][CH:24]=3)[CH:14]=[N:15][CH:16]=2)[N:11]=1)=[O:9]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 589795838-Bromo-[1,6]naphthyridine-2-carboxylic acid (furan-2-ylmethyl)-amide

Product 1

HCID 58979590HCID 58979590, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Compound 3 (above, 1 equiv.), 5-(dihydroxylboryl)-2-thiophene carboxylic acid (1 equiv.), dichloro(bistriphenylphosphine)palladium (II) (0.02 equiv.), and sodium carbonate (1.5 equiv.) are combined with 7:3:2; DME:water:methanol (4 mL) in a microwavable reaction tube. The reaction mixture is irradiated in the microwave at 140° C. for 300 seconds and then cooled to room temperature. The crude mixture is concentrated in vacuo, affording a green-brown solid. Purification via silica gel chromatography (EtOAc to 4:1; EtOAc:methanol containing 1% acetic acid) affords a bright yellow solid. LC/MS (M+H) 340.2.

Workup

  1. customThe reaction mixture is irradiated in the microwave at 140° C. for 300 seconds
  2. concentrationThe crude mixture is concentrated in vacuo
  3. customaffording a green-brown solid
  4. customPurification via silica gel chromatography (EtOAc to 4:1; EtOAc:methanol containing 1% acetic acid)
  5. customaffords a bright yellow solid

Sources & evidence

ORD record
ord-fe96a0676adb46acb8b3c99df2413b00
Source dataset
uspto-grants-2007_10
Patent number
US07282506B2

Reaction notes

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