1,2-Dichloroethane → HCID 59359760, compound

HRID 1187270Notes

Reaction equation

HRID 1187270 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[N:42]1([CH2:47][CH2:48][NH2:49])[CH2:46][CH2:45][CH2:44][CH2:43]1>C(Cl)Cl.CCOC(C)=O>[N:42]1([CH2:47][CH2:48][NH:49][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]3)=[CH:17][CH:16]=2)[CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 13441-PyrrolidineethanamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 59359760HCID 59359760, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (248.1 mg, 1 mmol), EDC (191.7 mg, 1 mmol) and HOBt (135.1 mg, 1 mmol) in DCM (3 mL), was added diisopropylethylamine (DIEA) (0.26 ml, 1.5 mmol). After stirring vigorously for 0.5 hours, 2-pyrrolidin-1-yl-ethylamine (0.15 ml, 1.2 mmol) was added. The mixture was stirred overnight, diluted with EtOAc (20 ml) and washed twice with brine. The organic layer was dried with sodium sulfate and concentrated to provide the crude product (230 mg, 66.8% yield), which used without further purification.

Workup

  1. stirringThe mixture was stirred overnight
  2. washwashed twice with brine
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a0cc4df802c44189690550020b139f8
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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