Dichloromethane → HCID 86664392, compound

HRID 1626419Notes

Reaction equation

HRID 1626419 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 1,2-dichloroethane (10 mL) was added 2 M solution of oxalyl chloride in dichloromethane (1.556 ml, 3.113 mmol) and the mixture was stirred at ambient temperature for 1 hour. Gas evolution was observed. 6-Bromopyridin-2-amine (0.489 g, 2.8303 mmol) and triethylamine (0.789 ml, 5.66 mmol) were added to the acid chloride solution. The mixture was stirred at ambient temperature for 18 hours. The whole mixture was purified on silica gel (EtOAc/hexanes gradient) to provide 0.939 g of the title compound as a white solid (65.3%). MS (apci) m/z=508.0 (M+H).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 18 hours
  2. customThe whole mixture was purified on silica gel (EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-2d550524fa564103a8b2b4dcc2b161b4
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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