1,2-Dichloroethane → HCID 59429624, compound

HRID 505086Notes

Reaction equation

HRID 505086 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[NH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([C:41]2[C:49]3[C:44](=[CH:45][C:46]([Cl:50])=[CH:47][CH:48]=3)[NH:43][CH:42]=2)=[O:40])[CH2:35][CH2:34]1>C(Cl)Cl>[Cl:50][C:46]1[CH:45]=[C:44]2[C:49]([C:41]([C:39]([N:36]3[CH2:35][CH2:34][CH:33]([NH:32][C:4](=[O:6])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[F:1])[CH2:38][CH2:37]3)=[O:40])=[CH:42][NH:43]2)=[CH:48][CH:47]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 99352-Fluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 66744376HCID 66744376, compound

Product 1

HCID 59429624HCID 59429624, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 50 mg (0.36 mmol) 2-fluoro-benzoic acid in 5 ml CH2Cl2 were added 90 mg (0.47 mmol) EDC, 63 mg (0.47 mmol) HOBt, 60 μl (0.47 mmol) Et3N and 100 mg (0.36 mmol) (4-amino-piperidin-1-yl)-(6-chloro-1H-indol-3-yl)-methanone. The mixture was stirred overnight at RT and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 82 mg (57%) N-[1-(6-Chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-2-fluoro-benzamide of as a white solid.

Workup

  1. additionpoured onto water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3b5513ab01743d6befc103423c1741a
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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