Dichloromethane → Ammonium Hydroxide

HRID 1661639Notes

Reaction equation

HRID 1661639 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:9](C)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.ClCCl.ClS([N:25]=[C:26]=O)(=O)=[O:23]>CN(C=O)C>[NH4+:5].[OH-:23].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([C:16]=1[C:26]#[N:25])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 70918Chlorosulfonyl isocyanateHCID 58215561HCID 58215561, compound

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 67093525HCID 67093525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask is charged with 2-(4-chloro-pyridin-3-yl)-1-methyl-1H-indole (Example 107, 0.110 g, 0.418 mmol) and dichloromethane (5 mL). Chlorosulfonyl isocyanate (0.091 mL, 1.04 mmol) is added and the reaction is stirred for 2 min, whereupon DMF (1 mL) is added. After another 20 min, the reaction is concentrated in vacuo and the residue is purified by reverse phase HPLC with Xbridge Shield RP18 column and a 0.1% aqueous NH4OH in acetonitrile gradient to afford 2-(4-chloro-pyridin-3-yl)-1H-indole-3-carbonitrile as a solid. 1H NMR (400 MHz, MeOD) δ ppm 3.74 (s, 3H), 7.41 (t, J=7.6 Hz, 1H), 7.49 (t, J=7.7 Hz, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.84 (d, J=5.3 Hz, 1H), 8.61-8.86 (m, 2H). HRMS (ESI) m/z 268.0635 [(M+H)+ Calcd for C15H11ClN3: 268.0641].

Workup

  1. additionis added
  2. concentrationthe reaction is concentrated in vacuo
  3. customthe residue is purified by reverse phase HPLC with Xbridge Shield RP18 column

Sources & evidence

ORD record
ord-96c4f38d02d543919039f8bb8bd053fa
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

Loading…