Dichloromethane → HCID 86664392, compound

HRID 1626397Notes

Reaction equation

HRID 1626397 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].C(Cl)(=O)C(Cl)=O.ClCCl.[Br:36][C:37]1[N:42]=[C:41]([NH2:43])[CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>ClCCCl.CN(C=O)C>[Br:36][C:37]1[N:42]=[C:41]([NH:43][C:18]([C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:8][O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:22][CH:21]=2)=[O:20])[CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 3008092-Amino-6-bromopyridineHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

Product 1

HCID 86664392HCID 86664392, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (1.00 g, 2.83 mmol) and a drop of DMF in DCE (10 ml) was added oxalyl chloride in dichloromethane (2M) (1.55 mL, 3.11 mmol). After stirring for 1 hour, 6-bromopyridin-2-amine (0.489 g, 2.83 mmol) and triethylamine (0.788 mL, 5.66 mmol) were added. After stirring overnight, the reaction was loaded onto silica gel and the product eluted to provide the desired product (0.939 g, 65%).

Workup

  1. stirringAfter stirring overnight
  2. washthe product eluted

Sources & evidence

ORD record
ord-6b80ad61fa3447d8949605515dbbec5a
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…