1,2-Dichloroethane → 4-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamide

HRID 2420726Notes

Reaction equation

HRID 2420726 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[NH:5][CH:6]=1.[NH2:10][C:11]1[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>ClC(Cl)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:10][C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]([OH:19])([CH3:20])[CH3:18])=[C:13]([O:23][CH3:24])[CH:12]=2)=[O:9])[NH:5][CH:6]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27413814-bromo-1H-pyrrole-2-carboxylic acidHCID 595950521-(4-Amino-2-methoxyphenoxy)-2-methylpropan-2-ol

Product 1

HCID 672152534-Bromo-N-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-1H-pyrrole-2-carboxylic acid (1.00 g, 5.30 mmol), preparation described in step A of Example 2, and 1-(4-amino-2-methoxyphenoxy)-2-methylpropan-2-ol (1.12 g, 5.30 mmol), preparation described in step A of Example 4. in dichloroethane (46.0 mL) was added EDC (2.03 g, 10.6 mmol) and HOBT (1.62 g, 10.6 mmol) and the reaction was allowed to stir at rt for 16 h. The reaction mixture was diluted with EtOAc (100 mL), washed with sat.

Workup

  1. washwashed with sat.

Sources & evidence

ORD record
ord-20c86ecd0f894f92a037f438a445af84
Source dataset
uspto-grants-2011_06
Patent number
US07956049B2

Reaction notes

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