Dichloromethane → Ammonium Hydroxide

HRID 593594Notes

Reaction equation

HRID 593594 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-e00d1af70dcc4f5bac4091d101da1a78
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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